Hydrochloric Acid → 4-Cyano-3-nitrobenzoic acid

HRID 1943112Notes

Reaction equation

HRID 1943112 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.[OH-].[Na+].Cl>O1CCCC1.O>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:15])=[O:2])=[CH:5][C:6]=1[N+:12]([O-:14])=[O:13])#[N:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53419688Methyl 4-cyano-3-nitrobenzoate

Product 1

HCID 221685834-Cyano-3-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

4-Cyano-3-nitro-benzoic acid methyl ester (13.4 g, 61.6 mmol) was dissolved in tetrahydrofuran (74 ml) and aqueous sodium hydroxide (1M) (73.9 ml) was added. The reaction mixture was stirred at 25° C. for 4 hours. Then the reaction mixture was diluted with water (700 ml) and acidified with aqueous hydrochloric acid (1M). The mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. 4-Cyano-3-nitro-benzoic acid (12.0 g) was used in the next step without further purification. 1H-NMR (400 MHz, DMSO-d6): 13.00 (bs, 1H), 8.79 (s, 1H), 8.40 (d, 1H), 8.30 (d, 1H) ppm.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated
  4. custom4-Cyano-3-nitro-benzoic acid (12.0 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-63532adad48e4395a51ba9fc5f66b21c
Source dataset
uspto-grants-2013_03
Patent number
US08389766B2

Reaction notes

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