Formic Acid → 4-(3-(Dimethylamino)propoxy)aniline

HRID 723342Notes

Reaction equation

HRID 723342 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1.C(O)=O>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 10353575N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

Product 1

HCID 100584694-(3-(Dimethylamino)propoxy)aniline

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Palladium(II) hydroxide (20% on carbon; 0.4 g) was added to a solution of dimethyl-[3-(4-nitrophenoxy)propyl]amine (3.75 g) in ethanol (75 ml) under argon. Then formic acid (4 ml) was added dropwise, during which the reaction mixture heated to 60° C. while evolving much gas. After a reaction time of 90 minutes, the catalyst was filtered off and the filtrate was concentrated. The residue was partitioned between methyl tert-butyl ether and sodium hydroxide solution (2N). The organic phase was dried and concentrated. The product with the molecular weight of 194.28 (C11H18N2O); MS (ESI):195 ([M+H]+), was obtained in this way.

Workup

  1. filtrationAfter a reaction time of 90 minutes, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between methyl tert-butyl ether and sodium hydroxide solution (2N)
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customMS (ESI):195 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-abea782cf2de4d93806b02fd7128ddc3
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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