4-Hydroxybenzaldehyde → HCID 54514261, compound

HRID 266409Notes

Reaction equation

HRID 266409 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10])[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][C:3]=1[C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1.O[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10])[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][C:3]=1[C:20]1[CH:28]=[CH:27][C:23]([C:24]([O:26][C:30]2[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 86751110HCID 86751110, compound

Product 1

HCID 54514261HCID 54514261, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.6 g of N,N'-dicyclodicyclohexylcarbodiimide was added at room temperature while stirring to a solution of 1.0 g of 4-[4-(2-amino-5-nitro-4-[(S)-2-octyloxy]phenyl)benzoic acid, 0.3 g of 4-hydroxybenzaldehyde and 0.04 g of 4-dimethylaminopyridine in 20 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of dichloromethane each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate was subsequently concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which were pure according to thin-layer chromatography gave 0.9 g of 4-[4-(2-amino-5-nitro-4-[(S)-2-octyloxy]phenyl)benzoyloxy]benzaldehyde; m.p. (C-I) 77°-78° C.

Workup

  1. addition0.6 g of N,N'-dicyclodicyclohexylcarbodiimide was added at room temperature
  2. extractionextracted three times with 50 ml of dichloromethane each time
  3. washThe organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was subsequently concentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which

Sources & evidence

ORD record
ord-286696e46b604c929b3c43c0167ae1f1
Source dataset
uspto-grants-1997_07
Patent number
US05650534

Reaction notes

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