Hydrazine, dihydrochloride → HCID 22037820, compound

HRID 1790018Notes

Reaction equation

HRID 1790018 reaction equation
[CH:1]1([N:6]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]2[CH:13]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl.[NH2:17][NH2:18]>C(O)C>[CH:1]1([N:6]2[C:7]3=[CH:13][N:17]=[N:18][C:11]([NH2:12])=[C:8]3[CH:9]=[CH:10]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 22037831HCID 22037831, compound

Product 1

HCID 22037820HCID 22037820, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyclopentyl-2-formyl-1H-3-pyrrolecarbonitrile (0.525 g, 2.79 mmol) and hydrazine dihydrochloride (0.35 g, 3.35 mmol) in ethanol (30 mL) was heated at reflux for 2.5 hours then cooled to ambient temperature and purified by preparative reverse phase HPLC to give the title compound as a hydroscopic glass contaminated with ammonium acetate (594 mg) (60% by weight as determined by 1H NMR, yield=337 mg; 1H NMR (DMSO-d6, 400 MHz) δ 8.83 (s, 1H), 7.55 (d, 1H), 6.71 (d, 1H), 6.10 (bs, 2H), 4.94 (m, 1H), 2.15 (m, 2H), 1.89 (m, 4H), 1.70 (m, 2H); 5%–100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 19.46 min.; LC/MS: MH+ 203.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-3ea04bd552ac4d0fbd04f91758f9a726
Source dataset
uspto-grants-2006_07
Patent number
US07071199B1

Reaction notes

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