Compounds derived from nitroacetic acids
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HYDROXYACETOPHENONES
Chapter 8. Compounds derived from nitroacetic acids 1-(3,5-Dichloro-2-hydroxyphenyl)-2-nitroethanone [60795-15-5]
C8H5Cl2NO4 Synthesis
OH COCH 2NO2
Cl
mol.wt. 250.04
Cl
-Preparation by treatment of 6,8-dichloro-4-hydroxy-3-nitrocoumarin with 4% potassium hydroxide solution at r.t. for 24 h (85%) [1221]. m.p. 137° [1221]; IR [1221].
1-(3-Chloro-2-hydroxyphenyl)-2-nitroethanone [60795-09-7]
C8H6ClNO4 Synthesis
OH COCH 2NO2
Cl
mol.wt. 215.59
-Preparation by treatment of 8-chloro-4-hydroxy-3-nitrocoumarin with 4% potassium hydroxide solution at r.t. for 24 h (83%) [1221]. m.p. 103° [1221]; IR [1221].
1-(4-Chloro-2-hydroxyphenyl)-2-nitroethanone [60795-11-1]
C8H6ClNO4
mol.wt. 215.59
Synthesis
OH COCH 2NO2 Cl
-Preparation by treatment of 7-chloro-4-hydroxy-3-nitrocoumarin with 4% potassium hydroxide solution at r.t. for 24 h (73%) [1221]. m.p. 117-118° [1221]; IR [1221].
1-(5-Chloro-2-hydroxyphenyl)-2-nitroethanone [60795-14-4]
C8H6ClNO4 Syntheses
OH COCH 2 NO 2
Cl
mol.wt. 215.59
-Preparation by treatment of 6-chloro-4-hydroxy-3-nitrocoumarin with 4% potassium hydroxide solution at r.t. for 24 h (65%) [1221]. -Also refer to: [1134]. m.p. 112° [1221]; IR [1221].
COMPOUNDS DERIVED FROM NITROACETIC ACIDS
191
1-(2-Hydroxy-5-nitrophenyl)-2-nitroethanone [59507-91-4]
C 8H 6N 2O 6
mol.wt. 226.15
Synthesis
OH
-Preparation by heating a solution of 3,6-dinitro-4-hydroxycoumarin (m.p. 188°) in 10% aqueous sodium hydroxide at 65° for 2 h, then cooling and acidification with hydrochloric acid (91%) [145].
COCH2NO2
NO2
m.p. 160° [145];
1H
NMR [145].
1-(4-Hydroxyphenyl)-2-nitrosoethanone [143527-88-2]
C8H7NO3
OH
mol.wt. 165.15
Synthesis
OH
-Refer to: [1427].
COCH N OH
COCH2
NO
1-(2-Hydroxyphenyl)-2-nitroethanone [29378-60-7]
C8H7NO4
mol.wt. 181.15
Syntheses
OH
-Preparation by alkaline degradation of 4-hydroxy-3-nitrocoumarin [1407] — m.p. 177° (d) — with 5% sodium hydroxide, *for 1.5 h at 50-60° (95%) [145]; *for 24 h at 20°, (79%) [664], (75%) [1221]. -The same compound was isolated in reactions of either some coumarins or some chromenes with 5% sodium hydroxide for 1 h at r.t. or by heating at 90-95° (70-90%) [584]: COCH 2 NO 2
coumarins: 3-nitro-4-(pyridylamino)coumarin 3-nitro-4-(3-methyl-2-pyridylamino)coumarin 3-nitro-4-(4-methyl-2-pyridylamino)coumarin 3-nitro-4-(5-methyl-2-pyridylamino)coumarin 3-nitro-4-(6-methyl-2-pyridylamino)coumarin
m.p. 224-225° m.p. 227-229° m.p. 243-244° m.p. 225-226° m.p. 250-252°
chromenes: 2-Hydroxy-3-nitro-4-(3-methyl-2-pyridylimino)-4H-chromene 2-Hydroxy-3-nitro-4-(4-methyl-2-pyridylimino)-4H-chromene 2-Hydroxy-3-nitro-4-(5-methyl-2-pyridylimino)-4H-chromene 2-Hydroxy-3-nitro-4-(6-methyl-2-pyridylimino)-4H-chromene -Also refer to: [336] [552] [1045] [1134] [1135] [1220]. m.p. 106-107° [664], 106° [145], 105-106° [1221], 96-97° [584]; 1H NMR [145] [584] [1221], IR [145] [584] [1221].
m.p. 245-246° m.p. 250-252° m.p. 233-234° m.p. 274-275°
192
HYDROXYACETOPHENONES
1-(2-Hydroxy-3-methylphenyl)-2-nitroethanone [60795-08
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