Hydrochloric Acid → 4-[[4-(1-Methylethoxy)phenyl]methyl]benzenamine

HRID 2121015Notes

Reaction equation

HRID 2121015 reaction equation
[CH:1]([O:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl>[Pd].C(O)C>[CH:1]([O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10968072HCID 10968072, compound

Product 1

HCID 108684364-[[4-(1-Methylethoxy)phenyl]methyl]benzenamineYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(4-isopropoxybenzoyl)-nitrobenzene (14.0 g, 49.09 mmol) and 10% palladium on carbon (2.0 g) in a solution of ethanol (250 mL) and concentrated hydrochloric acid (30 mL) was hydrogenated at 50 psi in a Parr apparatus for 16 hours. The catalyst was removed by filtration through a Celite pad, and filtrate was concentrated in vacuo. The residue was diluted with ice cold water, basified with concentrated ammonium hydroxide solution, and extracted into ethyl acetate. The organic extracts were washed with water and brine, and dried (MgSO4). Removal of the solvent gave a thick oil which on crystallization from ethyl acetate/hexanes gave 4-(4-isopropoxybenzyl)-phenylamine (10.4 g, 87%) as a white solid, m.p. 92-93° C.; Analysis for C16H19NO: Calc.: C, 79.63; H, 7.94; N, 5.80; Found: C, 79.51; H, 7.92; N, 5.96. MS m/e (%): 241 (M+, 83).

Workup

  1. customThe catalyst was removed by filtration through a Celite pad, and filtrate
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with ice cold water
  4. extractionextracted into ethyl acetate
  5. washThe organic extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvent
  8. customgave a thick oil which
  9. customon crystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ac4d89397efe4b749f965e087f0dfa22
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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