HCID 178492049, compound → HCID 43270961, compound

HRID 1443838Notes

Reaction equation

HRID 1443838 reaction equation
CN(C)CC[N:5](C)[C:6]1[CH:7]=[C:8]([N:14]2[C:18](S)=NN=[C:15]2[C:20]2C=C(C(C)C)C(O)=C[C:21]=2O)[CH:9]=[CH:10][C:11]=1OC>CO.CCOC(C)=O.[Pd]>[CH3:18][N:14]([CH2:15][CH2:20][CH3:21])[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([NH2:5])[CH:7]=1

Participants

4

Reactant 1

HCID 178492049HCID 178492049, compound

Product 1

HCID 43270961HCID 43270961, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 9.0 g (40.1 mmol mmol) of (2-Methoxy-5-nitro-phenyl)-methyl-propyl-amine (4) in 200 mL of MeOH/EtOAc (1:1) containing 5% w/w of Pd—C (10%) was subjected to hydrogenation (1 atm, balloon) overnight. The contents of the flask were passed through a short pad of celite and washed with EtOAc. The filtrate was evaporated under reduced pressure to give 7.7 g (92%) of crude amine 4-Methoxy-N3-methyl-N3-propyl-benzene-1,3-diamine (5) of an oil.

Workup

  1. customwas subjected to hydrogenation (1 atm, balloon) overnight
  2. washwashed with EtOAc
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6283c08881984f199431bcfb50387acd
Source dataset
uspto-grants-2010_02
Patent number
US07662813B2

Reaction notes

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