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

HRID 1358801Notes

Reaction equation

HRID 1358801 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-7d64fc8f5171467c88fd463428febaf1
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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