Hydrazine hydrate (1:1) → 2-(2,4-dichlorophenyl)-3-methyl-1H-pyrrol-1-amine

HRID 1791151Notes

Reaction equation

HRID 1791151 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH:11]=[CH:12][C:13]=1[CH3:14].O.NN>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]([NH2:15])[CH:11]=[CH:12][C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 220281732-[2-(2,4-dichlorophenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 220281722-(2,4-dichlorophenyl)-3-methyl-1H-pyrrol-1-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-[2-(2,4-dichlorophenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione (3.71 g, 10.0 mmol) in EtOH (60.0 mL) is added hydrazine monohydrate (1.21 mL, 1.25 g, 25.0 mmol) at room temperature. The reaction mixture is heated at reflux for 2 h. After cooling down to room temperature, the mixture is filtered. The filtrate is concentrated in vacuo to dryness and the residue is subjected to column chromatography (silica gel, 1/4 EtOAc/heptane) to give 2.36 g (98%) of light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.57 (d, J=2.1 Hz, 1H), 7.37 (dd, J=2.1, 8.2 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 6.82 (d, J=2.8 Hz, 1H), 6.01 (d, J=2.8 Hz, 1H), 2.00 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 136.5, 135.0, 134.6, 130.0, 129.9, 127.6, 127.3, 122.8, 117.0, 106.9, 12.3; IR (liq.) 2422, 2350, 2327, 2286, 2211, 1563, 1547, 1484, 1102, 1001, 868, 826, 806, 724, 708 cm-−1; MS (EI) m/z 243 (M++H), 241 (M++H); HRMS (FAB) calcd for C11H10Cl2N2+H 241.0299, found 241.0291.

Workup

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

Sources & evidence

ORD record
ord-a48105930d4e48379b8a71afc60b946d
Source dataset
uspto-grants-2006_07
Patent number
US07074791B2

Reaction notes

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