Acetic Acid → 2-Amino-4-fluoro-6-methylbenzonitrile

HRID 17549Notes

Reaction equation

HRID 17549 reaction equation
C(O)(=O)C.Cl.O.O.[Sn](Cl)(Cl)(Cl)Cl.[F:13][C:14]1[CH:21]=[C:20]([N+:22]([O-])=O)[C:17]([C:18]#[N:19])=[C:16]([CH3:25])[CH:15]=1.[OH-].[Na+]>CO>[NH2:22][C:20]1[CH:21]=[C:14]([F:13])[CH:15]=[C:16]([CH3:25])[C:17]=1[C:18]#[N:19]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 544206034-Fluoro-2-methyl-6-nitrobenzonitrileHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 450790392-Amino-4-fluoro-6-methylbenzonitrileYield 104.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (16.0 ml, 28 mmol) was added to a concentrated hydrochloric acid (90 ml) solution of tin chloride dihydrate (63.1 g, 280 mmol), and 4-fluoro-2-methyl-6-nitrobenzonitrile (I-263) (16.8 g, 93.3 mmol) was added, then methanol (8 ml) was added. Since the reaction liquid greatly generated heat, it was cooled with ice. After stirring for 1 hour, the reaction mixture liquid was poured into aqueous sodium hydroxide solution (4.6 M, 500 ml) with ice therein. The precipitated solid was collected by filtration, washed with water, then dried to obtain the entitled compound (14.7 g, 99%) as a gray solid.

Workup

  1. additionwas added
  2. customSince the reaction liquid
  3. temperaturegreatly generated heat
  4. temperatureit was cooled with ice
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-234628892ac14dcf83801d1683fe9b29
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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