Cyclopropanemethanamine → Methyl 4-[(cyclopropylmethyl)amino]-3-nitrophenylcarbamate

HRID 1796488Notes

Reaction equation

HRID 1796488 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[O:10][CH3:11])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH:16]1([CH2:19][NH2:20])[CH2:18][CH2:17]1>C(O)C>[CH:16]1([CH2:19][NH:20][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[O:10][CH3:11])=[CH:4][C:3]=2[N+:13]([O-:15])=[O:14])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 75646CyclopropanemethanamineHCID 3636899Methyl (4-fluoro-3-nitrophenyl)carbamate

Product 1

HCID 22181376Methyl 4-[(cyclopropylmethyl)amino]-3-nitrophenylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Following general procedure 2B: To methyl 4-fluoro-3-nitrophenylcarbamate (6.50 g, 30.35 mmol, from previous step) in 80% aqueous ethanol (100 mL) was added cyclopropanemethylamine (5.00 mL, 57,65 mmol) at room temperature. The reaction mixture was heated at 60° C. overnight. After the usual work up, the crude product, which precipitated out, was collected (8.21 g). MS (ESI) (M+H)+=266.

Workup

  1. customAfter the usual work up, the crude product, which precipitated out
  2. customwas collected (8.21 g)

Sources & evidence

ORD record
ord-5c3187edb35b4e3d91100710c278924a
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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