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

HRID 2383121Notes

Reaction equation

HRID 2383121 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20](Cl)=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O[NH:31][CH2:32][CH:33]([CH3:35])[CH3:34].C[OH:37]>>[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:31][CH2:32][C:33]([CH3:35])([OH:37])[CH3:34])=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=[N:23]2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 9543329N-(2-methylpropyl)hydroxylamineHCID 210757517-(Benzyloxy)-4-chloro-3-nitroquinoline

Product 1

HCID 670510171-(7-Benzyloxy-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol

Procedure

Triethylamine (81.3 g, 0.803 mol) was added to a solution of 230.0 g (0.731 mol) of 7-benzyloxy-4-chloro-3-nitroquinoline (230.0 g, 0.731 mmol), prepared in Parts A-D of Example 1, in methanol (1.84 L). Hydroxyisobutylamine (71.6 g, 0.803 mol) was then added over a period of five minutes; the temperature rose from 30° C. to 39° C. during the addition. The reaction mixture was heated at reflux for four hours and then allowed to cool to room temperature. The solid product was isolated by filtration, washed with ethanol (1 L), and dried under vacuum at 55° C. to provide 261.2 g of 1-[(7-benzyloxy-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol.

Workup

  1. additionthe temperature rose from 30° C. to 39° C. during the addition
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for four hours
  4. customThe solid product was isolated by filtration
  5. washwashed with ethanol (1 L)
  6. customdried under vacuum at 55° C.

Sources & evidence

ORD record
ord-22d966f480754080856f2979703e8e13
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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