Water → HCID 66814346, compound

HRID 1097601Notes

Reaction equation

HRID 1097601 reaction equation
C(N(CC)CC)C.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21](Cl)=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=[N:24]2)=[CH:19][CH:18]=1.O>CN(C=O)C>[CH2:8]([NH:15][C:21]1[C:20]2[C:25](=[CH:26][C:17]([Br:16])=[CH:18][CH:19]=2)[N:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 8471TriethylamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 66814346HCID 66814346, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (5.24 g, 51.8 mmol) and benzylamine (4.15 mL, 38.0 mmol) were sequentially added to a solution of 7-bromo-4-chloro-3-nitroquinoline (10.0 g, 34.5 mmol, see U.S. Patent Publication Application No. US 2004/0147543 (Hays et al.), Example 1 Parts A through D) in DMF (100 mL). The reaction was stirred at room temperature for three days, poured into water (800 mL), and stirred vigorously for 20 minutes. A precipitate formed and was isolated by filtration, washed with diethyl ether (800 mL), and dried under vacuum for four hours to provide 10.98 g of N-benzyl-7-bromo-3-nitroquinolin-4-amine as a yellow solid.

Workup

  1. stirringstirred vigorously for 20 minutes
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. washwashed with diethyl ether (800 mL)
  5. customdried under vacuum for four hours

Sources & evidence

ORD record
ord-c27718ef567443bd85c179792d380f95
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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