HCID 23139476, compound → 4-(3-dimethylamino-propoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

HRID 540631Notes

Reaction equation

HRID 540631 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16]1[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=1.[H][H]>CO.[Pd]>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:16]1[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 23139476HCID 23139476, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 231395434-(3-dimethylamino-propoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamineYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dimethyl-{3-[2-(2-methyl-2H-pyrazol-3-yl)-4-nitro-phenoxy]-propyl}-amine (1.4047 g, 4.62 mmol) and 5% Pd/C (114 mg) were stirred in methanol (50 mL) under 1 atm of hydrogen for 75 minutes. The suspension was filtered through celite and dried in vacuo to afford 4-(3-dimethylamino-propoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine as an orange oil (1.27 g, 100%).

Workup

  1. filtrationThe suspension was filtered through celite
  2. customdried in vacuo

Sources & evidence

ORD record
ord-53e39797c43545f1ae238fffd590cff1
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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