Methanol → 3-Cyano-2-methyl-6-[(phenylsulfonyl)amino]benzoic acid

HRID 1725890Notes

Reaction equation

HRID 1725890 reaction equation
[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([C:16]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:17][CH:18]=1)[C:6]([O:8]CC1C=CC=CC=1)=[O:7])#[N:2].CO>[Pd].C1COCC1>[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([C:16]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:21])=[O:22])=[CH:17][CH:18]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 68865363Benzyl 3-cyano-2-methyl-6-[(phenylsulfonyl)amino]benzoate

Product 1

HCID 688625433-Cyano-2-methyl-6-[(phenylsulfonyl)amino]benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 108C (140 mg, 0.34 mmol), 10% Pd/C (73 mg, 0.03 mmol), methanol (4 mL), and THF (8 mL) was stirred under a hydrogen atmosphere for 45 minutes and filtered. The filtrate was concentrated to an oil which was triturated with diethyl ether to provide the desired product. MS (ESI(−)) m/e 315 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.80 (m, 2H), 7.56 (m, 4H), 7.22 (d, 1H), 3.32 (br s, 2H), 2.56 (s, 3H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to an oil which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-7254b1d62aee4c79adcb9e77d1861a89
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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