Cyclopropanemethanamine → 4-((Cyclopropylmethyl)amino)-3-nitrobenzonitrile

HRID 1796474Notes

Reaction equation

HRID 1796474 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH:13]1([CH2:16][NH2:17])[CH2:15][CH2:14]1>C(O)C>[CH:13]1([CH2:16][NH:17][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 221812654-((Cyclopropylmethyl)amino)-3-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Following the general procedure 2B, 733 mg (4.42 mmol) of 4-fluro-3-nitrobenzonitrile in 80% aqueous ethanol (20 mL) was added cyclopropylmethylamine (377 mg, 5.3 mmol) at room temperature. The mixture was stirred at 60° C. for 3 h before work-up. The crude product (920 mg, 96%) was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 8.52 (s, 1H), 8.51–8.47 (br, 1H), 7.59 (d, J=8.4 Hz, 1H), 6.90 (d, J=8.4 Hz, 1H), 3.22–3.20 (m, 2H), 1.25–1.15 (m, 1H), 0.73–0.59 (m, 2H), 0.42–0.35 (m, 2H). MS (ESI) [2×(M+H)+]: 436.

Workup

  1. customThe crude product (920 mg, 96%) was used for the next step without further purification

Sources & evidence

ORD record
ord-96ef4f1f5b7d412681ae3339af7c453c
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

Loading…