Dichloromethane → HCID 67050960, compound

HRID 598295Notes

Reaction equation

HRID 598295 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25])=[C:14]([N+:19]([O-])=O)[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl>CO.[Pt]>[NH2:19][C:14]1[CH:15]=[N:16][C:17]2[C:12]([C:13]=1[NH:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25])=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:18]=2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 670510171-(7-Benzyloxy-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol

Product 1

HCID 67050960HCID 67050960, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-[(7-benzyloxy-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol (245.0 g, 0.667 mol) in methanol (3 L) was added to a pressure vessel containing 5% platinum on carbon (7.35 g). The vessel was placed under hydrogen pressure (30 psi, 2.1×105 Pa) at 55° C. for five hours. The reaction was allowed to cool to 40° C., and dichloromethane (2.5 L) was added. The reaction mixture was then filtered through CLARCEL filter aid at 30-40° C., and the filter cake was washed with methanol. The filtrate was concentrated to a volume of 1.5 L, cooled to 5-10° C., and stirred for two hours. A solid formed and was isolated by filtration, washed with a small amount of methanol, and dried under vacuum at 50° C. to provide 199.4 g of 1-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-2-methylpropan-2-ol.

Workup

  1. customat 55° C.
  2. customfor five hours
  3. filtrationThe reaction mixture was then filtered through CLARCEL
  4. filtrationfilter aid at 30-40° C.
  5. washthe filter cake was washed with methanol
  6. concentrationThe filtrate was concentrated to a volume of 1.5 L
  7. temperaturecooled to 5-10° C.
  8. customA solid formed
  9. customwas isolated by filtration
  10. washwashed with a small amount of methanol
  11. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-76151a2f10814a7fa414e76b5d8128df
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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