Carbon Tetrachloride → 8-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrile

HRID 379115Notes

Reaction equation

HRID 379115 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:12]2[C:21]3[C:16](=[C:17]([CH3:25])[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]=[CH:14][C:13]=2[C:26]#[N:27])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:28]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.S(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:28][CH2:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[C:21]2[C:16]=1[N:15]=[CH:14][C:13]([C:26]#[N:27])=[C:12]2[N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9](=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 224667474-[(3-Bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrileHCID 23665763Sodium Bisulfite

Product 1

HCID 224666528-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrileYield 119%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 4-[(3-bromophenyl)-N-acetylamino]-8-methyl-6-nitro-quinoline-3-carbonitrile (10.6 g, 25 mmol), N-bromosuccinimide (6.68 g, 37.5 mmol), 0.30 g of dibenzoyl peroxide, and 200 ml of carbon tetrachloride was refluxed for 2 h, treated with an additional 0.30 g of dibenzoyl peroxide, and refluxed an additional 2.5 h, cooled, diluted with methylene chloride, and stirred with aqueous sodium bisulfite. The organic layer was separated and washed successively with water, sodium bicarbonate solution, and water. The solution was dried and evaporated to give 15 g of a white foam, NMR (CDCl3) d 5.19 (dd, CH2Br).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturerefluxed an additional 2.5 h
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed successively with water, sodium bicarbonate solution, and water
  6. customThe solution was dried
  7. customevaporated

Sources & evidence

ORD record
ord-b4a50898b65e4d50961de3be23819a7e
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

Loading…