Triethylamine → 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N'-(2-chloroacetyl)hydrazide

HRID 644075Notes

Reaction equation

HRID 644075 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19](O)=[O:20])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[Cl:28][CH2:29][C:30]([NH:32][NH2:33])=[O:31].C(N(CC)CC)C>ClCCl>[Cl:28][CH2:29][C:30]([NH:32][NH:33][C:19]([C:10]1[C:11]2[C:16](=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[N:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:9]=1)=[O:20])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 101883Chloroacetyl hydrazineHCID 686950531-(Cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid

Product 1

HCID 686955621-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N'-(2-chloroacetyl)hydrazideYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid (1.0 g, 3.48 mmol) in dichloromethane (20 ml) was added oxalyl chloride (0.6 ml, 6.96 mmol) and the reaction stirred for 3.5 h. The solvent was evaporated under reduced pressure and the resulting residue redissolved in dichloromethane (20 ml). To the solution was added chloroacetic acid hydrazide (1.3 g, 8.97 mmol) and triethylamine (2.9 ml, 20.9 mmol) and the reaction mixture stirred for 4 h and then left to stand overnight. The solvent was evaporated under reduced pressure and the resulting residue purified by flash column chromatography eluting with 50-100% (v/v) ethyl acetate in heptane to give 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N′-(2-chloroacetyl)hydrazide (397 mg, 1.05 mmol).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe resulting residue redissolved in dichloromethane (20 ml)
  3. stirringthe reaction mixture stirred for 4 h
  4. waitleft
  5. waitto stand overnight
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue purified by flash column chromatography
  8. washeluting with 50-100% (v/v) ethyl acetate in heptane

Sources & evidence

ORD record
ord-7bbb6a21e680484fbec7fbb9d71cbee2
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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