Benzylamine → HCID 69057961, compound

HRID 1818068Notes

Reaction equation

HRID 1818068 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[N+:14]([C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[C:22]2[C:27]([OH:29])=O)([O-:16])=[O:15].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O.O1CCCC1>[CH2:30]([NH:37][C:27]([C:22]1[C:23]2[C:18](=[C:17]([N+:14]([O-:16])=[O:15])[CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1)=[O:29])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4589625-nitronaphthalene-1-carboxylic acid

Product 1

HCID 69057961HCID 69057961, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.16 ml, 1.15 mmol) and ethyl chloroformate (0.11 ml, 1.115 mmol) were added to a suspension of 5-nitronaphthalene-1-carboxylic acid (250 mg, 1.15 mmol) and anhydrous tetrahydrofuran (3 ml) under ice cooling, and the mixture was stirred for 0.5 hour. Benzylamine (0.13 ml, 1.20 mmol) was added to the reaction mixture and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution, and after the mixture was stirred for 10 minutes, the resulting precipitate was collected. The precipitate was washed with water and isopropyl ether, and dried to give the title compound as a light brown solid (189 mg, 53.5%).

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. stirringafter the mixture was stirred for 10 minutes
  3. customthe resulting precipitate was collected
  4. washThe precipitate was washed with water and isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-b0f74a4441334dafaab516296e6d364a
Source dataset
uspto-grants-2009_10
Patent number
US07598418B2

Reaction notes

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