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

HRID 1818155Notes

Reaction equation

HRID 1818155 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-e1accfaccbfd486495efc1f7efa9b0ae
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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