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

HRID 1818207Notes

Reaction equation

HRID 1818207 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-bede23847f854d9aa689be3226ba2428
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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