3-Hydroxy-4-nitrobenzaldehyde → [5-(1H-Indol-2-yl)-2-methoxy-phenyl]-(3-hydroxy-4-nitro-benzyl)-amine

HRID 25525Notes

Reaction equation

HRID 25525 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH2:28])[CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH:28][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([OH:1])[CH:3]=2)[CH:27]=1

Participants

7

Reactant 4

HCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99002045-(1H-indol-2-yl)-2-methoxy-phenylamine

Product 1

HCID 10221915[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-(3-hydroxy-4-nitro-benzyl)-amineYield 64.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-4-nitrobenzaldehyde (0.334 g, 2.0 mmol) was added to a stirred mixture of 5-(1H-indol-2-yl)-2-methoxy-phenylamine (0.476 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture is stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 3 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture is stirred for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give a brown gum. Recrystallization from methanol gave the product (500 mg), mp 134-135° C.

Workup

  1. stirringthe resulting homogeneous solution was stirred at room temperature for 3 days
  2. stirringthe mixture is stirred for 2 hours
  3. stirringThe mixture was shaken
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customto give a brown gum
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e41c0f00a96040ea89391dae25c37c8b
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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