4-Methoxy-3-nitrobenzonitrile → 3-Amino-4-methoxybenzonitrile

HRID 2185926Notes

Reaction equation

HRID 2185926 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([N+:9]([O-])=O)[CH:8]=1)#[N:2]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:8]=1)[NH2:9])#[N:2]

Participants

3

Reactant 1

HCID 28002414-Methoxy-3-nitrobenzonitrile

Product 1

HCID 224525573-Amino-4-methoxybenzonitrileYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.8 g of Compound 18A and 46.8 g of stannous chloride dihydrate in 250 mL of 95% ethanol was refluxed for 1 hour. The solvent was evaporated off in vacuo and the residue was taken up with 200 mL of water. The mixture was acidified with 37% HCl, then alkalinised with 35% sodium hydroxide and extracted with 3×200 mL of diethyl ether. The combined organic layers were washed with 50 mL of water, dried over sodium sulphate and evaporated to dryness in vacuo to afford 6.90 g (94.2%) of Compound 18B as an ivory solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customThe solvent was evaporated off in vacuo
  3. extractionextracted with 3×200 mL of diethyl ether
  4. washThe combined organic layers were washed with 50 mL of water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-57f4897fb02e4485a64ebc3cb255da9c
Source dataset
uspto-grants-2002_06
Patent number
US06403594B1

Reaction notes

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