HCID 21075825, compound → tert-butyl N'-(3-amino-7-benzyloxyquinolin-4-yl)hydrazinecarboxylate

HRID 1373957Notes

Reaction equation

HRID 1373957 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O: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>CO.C(#N)C.[Pt]>[NH2:19][C:14]1[CH:15]=[N:16][C:17]2[C:12]([C:13]=1[NH:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:18]=2

Participants

5

Reactant 1

HCID 21075825HCID 21075825, compound

Product 1

HCID 21075821tert-butyl N'-(3-amino-7-benzyloxyquinolin-4-yl)hydrazinecarboxylateYield 98.2%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl N′-(7-benzyloxy-3-nitroquinolin-4-yl)hydrazinecarboxylate (20.00 g, 48.73 mmol) in 200 mL of methanol and 200 mL of acetonitrile was treated with platinum on carbon (2.00 g, 0.51 mmol) and shaken under an atmosphere of hydrogen (3.8×105 Pa). After 17 h, the mixture was filtered through a pad of CELITE filter agent and rinsed with MeOH:MeCN (1:1) until the filtrate ran clear. The filtrate was concentrated under reduced pressure to yield 18.21 g of tert-butyl N′-(3-amino-7-benzyloxyquinolin-4-yl)hydrazinecarboxylate as a red/orange solid.

Workup

  1. filtrationthe mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with MeOH:MeCN (1:1) until the filtrate
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3698b74086114068a984f40bea75a445
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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