Isopropanol → HCID 21984278, compound

HRID 244861Notes

Reaction equation

HRID 244861 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18].C(O)(C)C>[Pt].C1(C)C=CC=CC=1>[NH2:12][C:6]1[CH:7]=[N:8][C:9]2[C:4]([C:5]=1[NH:15][CH2:16][C:17]([CH3:18])([OH:19])[CH3:20])=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 690795671-[(6-Bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol

Product 1

HCID 21984278HCID 21984278, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

1-[(6-Bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol (17.2 g, 50.5 mmol), toluene (150 mL) and isopropanol (20 mL) were added to a Parr flask containing 5% platinum on carbon (1.7 g) wetted with toluene. The flask was evacuated three times, charged with hydrogen to 30 psi, and shaken for 72 hours. The reaction mixture was filtered through a pad of CELITE filter agent. The CELITE was washed with several portions of dichloromethane followed by methanol. The filtrate was concentrated to provide crude 1-[(3-amino-6-bromoquinolin-4-yl)amino]-2-methylpropan-2-ol as a brown oil.

Workup

  1. customThe flask was evacuated three times
  2. additioncharged with hydrogen to 30 psi
  3. filtrationThe reaction mixture was filtered through a pad of CELITE
  4. filtrationfilter agent
  5. washThe CELITE was washed with several portions of dichloromethane
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8a43b6ad273c4d0c8c75920728e85587
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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