Methanol → Ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl)indol-1-yl}butanoate

HRID 1066176Notes

Reaction equation

HRID 1066176 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[O:7])=[CH:4][C:3]=1[OH:27].CO.[CH2:30]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[CH3:31].C([BH3-])#N.[Na+]>O.C(O)(=O)C>[CH2:30]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:1][C:2]2[CH:26]=[CH:25][C:5]([C:6]([C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=3)=[O:7])=[CH:4][C:3]=2[OH:27])=[CH:34][CH:33]=1)[CH3:31]

Participants

7

Reactant 4

HCID 887MethanolHCID 208614-EthylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21197991Ethyl 4-[3-(4-amino-3-hydroxybenzoyl)indol-1-yl]butanoate

Product 1

HCID 21197979Ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl)indol-1-yl}butanoateYield 81.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

Ethyl 4-[3-(4-amino-3-hydroxybenzoyl)indol-1-yl]butanoate (5.0 g) was suspended in a mixed solvent containing methanol (50 ml) and water (5 ml), and 4-ethylbenzaldehyde (3.66 g) and sodium cyanoborohydride (1.80 g) were added to the suspension. Acetic acid (2.5 ml) was further added dropwise to the mixture over five minutes, and the resultant mixture was stirred at room temperature for one hour. Water (50 ml) was added to the reaction mixture, and crystals so precipitated were collected by filtration. The produced crystals were recrystallized from ethanol, to thereby obtain 5.39 g of ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl)indol-1-yl}butanoate as yellow crystals.

Workup

  1. additionwere added to the suspension
  2. customso precipitated
  3. filtrationwere collected by filtration
  4. customThe produced crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-039bc53ae1604444a06c0ea80caa0d51
Source dataset
uspto-grants-2001_06
Patent number
US06242449B1

Reaction notes

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