Water → (1-Biphenyl-2-ylmethyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetic acid hydrazide

HRID 2292793Notes

Reaction equation

HRID 2292793 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][C:20]([NH2:22])=[O:21])=[C:9]1[CH3:23].C(OC(=O)CC1C2C(=CC=C(OC)C=2)[N:37](CC2C=CC=CC=2C2C=CC=CC=2)C=1C)C.NN.O>C(O)C>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][C:20]([NH:22][NH2:37])=[O:21])=[C:9]1[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 10500247HCID 10500247, compoundHCID 107642291-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester

Product 1

HCID 10834763(1-Biphenyl-2-ylmethyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetic acid hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-([1,1'-Biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetamide. A mixture of 1.18 g (2.86 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester and 3 mL of hydrazine in 20 mL of ethanol was heated to maintain reflux for 16 hours. After cooling, water was added and the mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4), and concentrated to give 1.02 g of 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid hydrazide. A mixture of 576 mg (1.44 mmol) of this material and 300 mg of Raney Ni in 20 mL of ethanol was heated to maintain reflux for 3 hours. After cooling the solvent was decanted and the Raney Ni washed twice with methylene chloride. The combined organic solvents were concentrated at reduced pressure and the residue chromatographed on silica gel and eluted with ethyl acetate to give 369 mg (67% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetamide.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 16 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-abc00abda5db4878873adf7bba1660ff
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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