HCID 13369965, compound → HCID 22329432, compound

HRID 246853Notes

Reaction equation

HRID 246853 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([N+:16]([O-])=O)[C:10]=1[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]1[C:10]([CH3:19])=[C:11]([C:12]([CH3:15])=[CH:13][CH:14]=1)[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 13369965HCID 13369965, compound

Product 1

HCID 22329432HCID 22329432, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust is added in portions to a solution of 4-benzyloxy-2-nitro-m-xylene (83.8 g) in glacial acetic acid (715 ml). Addition is complete when the exothermic reaction subsides. The reaction mixture is filtered through Celite and the pad washed with acetic acid. The filtrate is concentrated in vacuo and the residue diluted with H2O and made basic with ammonium hydroxide, and extracted with chloroform. The combined organic extracts are dried and concentrated in vacuo to give the desired aniline in quantitative crude yield.

Workup

  1. additionAddition
  2. customthe exothermic reaction subsides
  3. filtrationThe reaction mixture is filtered through Celite
  4. washthe pad washed with acetic acid
  5. concentrationThe filtrate is concentrated in vacuo
  6. additionthe residue diluted with H2O
  7. extractionextracted with chloroform
  8. customThe combined organic extracts are dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4ebe1c722544279a2e62d92798bfabe
Source dataset
uspto-grants-1987_11
Patent number
US04704401

Reaction notes

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