Triethylamine → Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate

HRID 1818235Notes

Reaction equation

HRID 1818235 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23](Cl)=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=[N:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl>[Br:18][C:19]1[CH:28]=[C:27]2[C:22]([C:23]([NH:17][CH2:16][C:13]3[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:11][CH:12]=3)=[C:24]([N+:29]([O-:31])=[O:30])[CH:25]=[N:26]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamateHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 21984421Tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamateYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(N-BOC-aminomethyl)-4-(aminomethyl)benzene (5.0 g, 21 mmol) in dichloromethane (50 mL) was added dropwise to a mixture of 7-bromo-4-chloro-3-nitroquinoline (5.81 g, 20 mmol) and triethylamine (5.63 mL) in dichloromethane (60 mL). The reaction was stirred for 16 hours and then washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered and concentrated to provide a yellow crystalline solid. Recrystallization from 2-propanol yielded 9.1 g of tert-butyl {4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate as a yellow powder.

Workup

  1. washwashed sequentially with water and saturated aqueous sodium chloride
  2. dry with materialThe organic fraction was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a yellow crystalline solid
  6. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-6ce583ace1ca4895b6dc0b4146493d91
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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