Hexane → 5-[N-(2-nitrobenzoyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637270Notes

Reaction equation

HRID 1637270 reaction equation
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.[N+:20]([C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26])([O-:22])=[O:21].C(N(CC)CC)C.CCCCCC>C(Cl)Cl>[N+:20]([C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([NH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1)=[O:26])([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Product 1

HCID 193481975-[N-(2-nitrobenzoyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (200 mg) of the compound obtained in Example 81 was suspended in methylene chloride (10 ml) and to the suspension were added 2-nitrobenzoyl chloride (0.18 ml) and triethylamine (0.11 ml) under cooling with ice. The mixture was stirred for 30 minutes at room temperature. n-Hexane was added to the reaction mixture, and the crystals were collected by filtration and washed with water and n-hexane successively to yield 260 mg (81%) of the titled compound as brown crystals.

Workup

  1. temperatureunder cooling with ice
  2. filtrationthe crystals were collected by filtration
  3. washwashed with water and n-hexane successively

Sources & evidence

ORD record
ord-993b8a9f247c4b5eb9a2be3335cdba78
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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