HCID 66620230, compound → HCID 66620332, compound

HRID 415554Notes

Reaction equation

HRID 415554 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>[Pt].C(OCC)(=O)C.ClCCl>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

5

Reactant 1

HCID 66620230HCID 66620230, compound

Product 1

HCID 66620332HCID 66620332, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A hydrogenation flask was charged with platinum on carbon (5%, 2 g) followed by a solution of tert-butyl 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propylcarbamate in ethyl acetate (200 mL) and dichloromethane (75 mL). The reaction mixture was shaken under H2 at 46 PSI (3.2×105 Pa) overnight and then filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure to give 9.3 g of tert-butyl 3-[(3-amino-7-bromoquinolin-4-yl)amino]propylcarbamate.

Workup

  1. filtrationfiltered through a layer of CELITE filter agent
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e26f171e04c74c4f9ddedd3e444db963
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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