Hydrochloric Acid → 4-Methoxy-3-propyl-5-(trifluoromethoxy)aniline--hydrogen chloride (1/1)

HRID 638932Notes

Reaction equation

HRID 638932 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([O:13][C:14]([F:17])([F:16])[F:15])[C:5]=1[O:18][CH3:19])[CH:2]=[CH2:3].[ClH:20]>CO.[Pd]>[ClH:20].[CH3:19][O:18][C:5]1[C:6]([O:13][C:14]([F:15])([F:17])[F:16])=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 686838692-Methoxy-5-nitro-1-(prop-2-en-1-yl)-3-(trifluoromethoxy)benzene

Product 1

HCID 686825024-Methoxy-3-propyl-5-(trifluoromethoxy)aniline--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 1-allyl-2-methoxy-5-nitro-3-trifluoromethoxybenzene (1.9 g, 6.86 mmol, 1 eq.) in MeOH (26 mL) at room temperature was added aqueous HCl solution (3.4 mL, 3.0 M) followed by 10% Pd/C (256 mg). The reaction mixture was stirred under H2 atmosphere for 17 h, filtered through a pad of celite and concentrated in vacuo to give 4-methoxy-3-propyl-5-trifluoromethoxyphenylamine hydrochloride (1.6 g). The product was used without further purification.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be80e9f097aa46f7aa976b0895ad5078
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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