Hydrazine hydrate (1:1) → 2-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-amine

HRID 1796963Notes

Reaction equation

HRID 1796963 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([N:15]3C(=O)C4C(=CC=CC=4)C3=O)[CH:11]=[CH:12][C:13]=2[CH3:14])=[C:5]([CH3:26])[CH:4]=1.O.NN>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([NH2:15])[CH:11]=[CH:12][C:13]=2[CH3:14])=[C:5]([CH3:26])[CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 221747872-[2-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 221747842-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-amineYield 93.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-[2-(4-methoxy-2-methylphenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione (0.40 g, 1.15 mmol) in EtOH was added hydrazine monohydrate (0.14 mL, 2.89 mmol) at room temperature. The reaction mixture was heated at reflux for 1 h. After cooling down to room temperature, the mixture was filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography (silica gel, 1/4 EtOAc/heptane) to give 0.233 g (93%) of clear oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8 Hz, 1H), 6.89 (s, 1H), 6.84–6.79 (m, 2H), 6.00 (s, 1H), 3.87 (s, 3H), 2.16 (s, 3H), 1.93 (s, 3H); MS m/z 217.1 (M++H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-42e60754c8844d04a095110fe7b72483
Source dataset
uspto-grants-2006_04
Patent number
US07034023B2

Reaction notes

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