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

HRID 9489
Notes
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Reaction equation

HRID 9489 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>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:23]2[C:22]3[C:27](=[CH:28][C:19]([Br:18])=[CH:20][CH:21]=3)[N:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])=[CH:12][CH:11]=1)([CH3:7])([CH3:6])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344Dichloromethane
Solvent
2×

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-e290789573584e50a29ba8fd5e830722
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091214B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes