Water → N-[4-(3-nitro-7-phenylquinolin-4-ylamino)butyl]methanesulfonamide

HRID 9405Notes

Reaction equation

HRID 9405 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:29]([O-:31])=[O:30].C(N(CC)CC)C.O>CN1C(=O)CCC1>[N+:29]([C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:13]=1[NH:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:21][CH:20]=[C:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:18]=2)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 21984197N-(4-aminobutyl)methanesulfonamide hydrochlorideHCID 219843354-Chloro-3-nitro-7-phenylquinoline

Product 1

HCID 21984203N-[4-(3-nitro-7-phenylquinolin-4-ylamino)butyl]methanesulfonamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-(4-aminobutyl)methanesulfonamide hydrochloride (7.8 g, 39 mmol) was added to a suspension of 4-chloro-3-nitro-7-phenylquinoline (35 mmol) and triethylamine (8.0 g, 79 mmol) in NMP (80 mL), and the reaction was stirred at ambient temperature overnight. The resulting solution was poured into water (350 mL) to form a solid, which was isolated by filtration, washed with water, air-dried, and recrystallized from acetonitrile to provide 12.0 g of N-[4-(3-nitro-7-phenylquinolin-4-ylamino)butyl]methanesulfonamide as yellow plates.

Workup

  1. customto form a solid
  2. customwhich was isolated by filtration
  3. washwashed with water
  4. customair-dried
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-8fccf99693c64fad9f96b1c8c8faeb9d
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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