Ammonium Chloride → 5-Amino-2-methoxybenzonitrile

HRID 429321Notes

Reaction equation

HRID 429321 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:4]=1[C:5]#[N:6].[Cl-].[NH4+]>CO>[C:5]([C:4]1[CH:7]=[C:8]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[NH2:11])#[N:6]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 826772-Methoxy-5-nitrobenzonitrile

Product 1

HCID 41026715-Amino-2-methoxybenzonitrileYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-methoxy-5-nitrobenzonitrile (14 g), ammonium chloride (5 g), the powder of reduced iron (9 g) in methanol was refluxed for 4 hours and cooled. The reaction mixture was filtered and the filtrate was poured into water. The resultant precipitates were filtered and washed with water to give 3-cyano-4-methoxyaniline (7.7 g).

Workup

  1. temperaturecooled
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was poured into water
  4. customThe resultant precipitates
  5. filtrationwere filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-bbf43b0b864d4afd93954892a585f6ac
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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