Phenylhydrazine → HCID 15032471, compound

HRID 1079381Notes

Reaction equation

HRID 1079381 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([C:10](=O)[C:11]([O:13]CC)=O)[C:2]1=[O:17].[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(=O)C>[C:18]1([N:24]2[C:2](=[O:17])[C:3]3[C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=4[NH:1][C:11](=[O:13])[C:10]=3[NH:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 372101ETHYL 2-OXO-3-INDOLINEGLYOXYLATE

Product 1

HCID 15032471HCID 15032471, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl oxindole-3-glyoxylate (220 rag) in glacial acetic acid (2 ml) was heated under reflux for 10 minutes with phenylhydrazine (0.1 ml). The reaction was cooled and the resulting precipitate filtered and crystallised from methanol to give the title compound, mp>260° C.; 1H nmr (250 MHz, d6 -DMSO) δ5 11.86 (1H, broad s), 8.25 (1H, broad d), 7.86 (2H, d, J=8 Hz), 7.56 (2H, t, J=8 Hz) and 7.22-7.42 (4H, m).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe resulting precipitate filtered
  3. customcrystallised from methanol

Sources & evidence

ORD record
ord-42244f29631944f58e7654295eec41e4
Source dataset
uspto-grants-1996_12
Patent number
US05580877

Reaction notes

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