Triethylamine → 1-(7-Benzyloxy-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol

HRID 2383169Notes

Reaction equation

HRID 2383169 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:30][CH2:31][C:32]([CH3:35])([OH:34])[CH3:33]>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:30][CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 670510171-(7-Benzyloxy-3-nitroquinolin-4-ylamino)-2-methylpropan-2-olYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Benzyloxy-4-chloro-3-nitroquinoline (66.4 g, 0.21 mol) was dissolved in a mixture of dichloromethane (1.5 L) and triethylamine (59 mL, 0.422 mol). A solution of 1-amino-2-methyl-2-propanol (22.5 g, 0.25 mol) in dichloromethane (100 mL) was added dropwise. The reaction was stirred at ambient temperature for 3 hours and then quenched with 1% aqueous sodium carbonate solution. A precipitate formed which was filtered to provide 60 g of crude 1-(7-benzyloxy-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol as a yellow-brown solid.

Workup

  1. customquenched with 1% aqueous sodium carbonate solution
  2. customA precipitate formed which
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-42c77b53272b4a13a656799909b4911b
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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