Triethylamine → 1-(6-Benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol

HRID 9458

Reaction equation

HRID 9458 reaction equation
[NH2:1][CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].[CH2:7]([C:14]1[CH:23]=[C:22]2[C:17]([C:18](Cl)=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[N:21]2)=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:28]([C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]=[CH:40][C:39]([N+:45]([O-:47])=[O:46])=[C:38]2Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>ClCCl>[CH2:7]([C:14]1[CH:23]=[C:22]2[C:17]([C:18]([NH:1][CH2:2][C:3]([CH3:6])([OH:5])[CH3:4])=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[N:21]2)=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[CH2:28]([C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]=[CH:40][C:39]([N+:45]([O-:47])=[O:46])=[C:38]2[NH:1][CH2:2][C:3]([CH3:6])([OH:5])[CH3:4])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 219841937-Benzyl-4-chloro-3-nitroquinolineHCID 219842266-Benzyl-4-chloro-3-nitroquinoline

Product 2

HCID 219844101-(6-Benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-olHCID 219844521-(7-Benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 1-amino-2-methylpropan-2-ol (1.2 equivalents) was added to a 0.2 M solution of 7-benzyl-4-chloro-3-nitroquinoline or 6-benzyl-4-chloro-3-nitroquinoline (1 equivalent) and triethylamine (3 equivalents) in dichloromethane, and the reaction was stirred overnight at ambient temperature. The volatiles were removed under reduced pressure, and the residue was stirred with water (50 mL) for one hour. The resulting yellow solid was isolated by filtration and washed with water to provide 1-(7-benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol or 1-(6-benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol, respectively.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. stirringthe residue was stirred with water (50 mL) for one hour
  3. customThe resulting yellow solid was isolated by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-a26247a753df407cb8aa5733bcc350c4
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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