Sodium Dithionite → 2-Amino-4,5-dimethoxybenzonitrile

HRID 466995Notes

Reaction equation

HRID 466995 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:1][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 15112884,5-Dimethoxy-2-nitrobenzonitrile

Product 1

HCID 7359672-Amino-4,5-dimethoxybenzonitrileYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-nitro-4,5-dimethoxybenzonitrile (6.0 g, 28.8 mmol) in water (200 mL) was heated to 90° C. To this hot mixture was added sodium dithionite in a small portion until it was dissolved completely. The resulting solution was filtered and then cooled to room temperature to get crystal. The solid was collected by filtration to afford 4.99 g (97%) of 2-amino-4,5-dimethoxybenzonitrile. An analytical sample was recrystallized from acetonitrile. 1H NMR (100 MHz, DMSO-d6): δ3.64 (s, 3H, CH3), 3.73 (s, 3H, CH3), 4.32 (br s, 2H, NH2), 6.41 (s, 1H, Ar--H), 6.86 (s, 1H, Ar--H). 13C NMR (25 MHz, DMSO-d6): d 55.55, 56.87, 83.67, 92.08, 113.96, 140.33, 148.12, 154.33. MS: m/z 178 (M+), 163 (M+ -15), 147 (M+ -31), 135 (M+ -43), 120 (M+ -58).

Workup

  1. dissolutionwas dissolved completely
  2. filtrationThe resulting solution was filtered
  3. temperaturecooled to room temperature
  4. customto get crystal
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-8cb6d4ea207f4edaaf77ca0d46072cf2
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Reaction notes

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