Benzylamine → 7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

HRID 274054

Reaction equation

HRID 274054 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:23]=[CH:22][C:15]2[CH2:16][CH2:17][CH:18]=[CH:19][C:20](=[O:21])[C:14]=2[CH:13]=1)([O-:11])=[O:10]>C1C=CC=CC=1.C(O)C>[CH2:1]([NH:8][CH:18]1[CH2:17][CH2:16][C:15]2[CH:22]=[CH:23][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][C:14]=2[C:20](=[O:21])[CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 200947328,9-dihydro-3-nitro-5H-benzocyclohepten-5-one

Product 1

HCID 200948737-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-oneYield 107.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A solution of benzylamine (8.18 g) in benzene (100 ml) was added dropwise to a suspension of 8,9-dihydro-3-nitro-5H-benzocyclohepten-5-one (15.51 g) in ethanol (155 ml) at ambient temperature over 20 minutes. The resulting mixture was stirred at the same temperature for 3 hours 30 minutes, allowed to stand at the same temperature overnight, and filtered. The filtrate was evaporated in vacuo to afford 7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (25.41 g) as a dark brown oil.

Workup

  1. customto stand at the same temperature overnight
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3614fa02fd3c42f88c534c7474abb3ef
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Linked notes

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