Triethylamine → (2-Amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amine

HRID 2076257Notes

Reaction equation

HRID 2076257 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][C:10]([NH2:13])([CH3:12])[CH3:11].[CH2:14]([O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26](Cl)=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[N:29]2)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[NH2:13][C:10]([CH3:12])([CH3:11])[CH2:9][NH:8][C:26]1[C:25]2[C:30](=[CH:31][C:22]([O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:23][CH:24]=2)[N:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 67050934(2-Amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amineYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (12.8 mL, 92.0 mmol) and 1,2-diamino-2-methylpropane (5.29 mL, 50.6 mmol) were added sequentially to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (14.5 g, 46.0 mmol) in dichloromethane (400 mL). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was partitioned between water (200 mL) and dichloromethane (300 mL). The organic layer was washed with brine, dried over sodium sulfate, and then concentrated under reduced pressure to provide crude product as a brown solid. The crude product was passed through a layer of silica gel (eluting sequentially with chloroform and 96:4 chloroform:methanol) to provide 12.4 g of (2-amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amine as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water (200 mL) and dichloromethane (300 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide crude product as a brown solid
  7. washeluting sequentially with chloroform and 96:4 chloroform

Sources & evidence

ORD record
ord-203274fc77614065bf7ebfdbf8f1176a
Source dataset
uspto-grants-2011_04
Patent number
US07923560B2

Reaction notes

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