Hydrochloric Acid → HCID 58551630, compound

HRID 1908081Notes

Reaction equation

HRID 1908081 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=[O:7])#[N:2].[OH:16]O.[OH-].[Na+].Cl>>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6]([OH:8])=[O:7])(=[O:16])[NH2:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 21956832RP-101124

Product 1

HCID 58551630HCID 58551630, compoundYield 84%

Procedure

3-Cyano-4-isopropoxy-benzoic acid (50 mg, 0.24 mmol), hydrogen peroxide (280 μL of 30% w/v, 2.4 mmol), and 10% NaOH (240 μL of 10% w/v, 0.61 mmol) were combined and stirred at room temperature for 16 h. The mixture was acidified with 4M HCl and was extracted with ethyl acetate (2×7 mL). The combined organics were washed with brine, dried over sodium sulfate and evaporated to give 3-carbamoyl-4-isopropoxy-benzoic acid (45 mg, 83%). ESI-MS m/z calc. 223.1. found 224.3 (M+1)+; Retention time: 1.49 minutes (4 min run).

Workup

  1. extractionwas extracted with ethyl acetate (2×7 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d791c76a80f54c0f928bdf075d6422cf
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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