Hydrochloric Acid → 3-(2-(Naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid

HRID 2097967Notes

Reaction equation

[C:1]1([CH2:11][C:12]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22]C)=[O:21])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1.O>[C:1]1([CH2:11][C:12]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([OH:22])=[O:21])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylate (210 mg, 0.645 mmol) was dissolved in THF/H2O (2.5 mL, 4/1, v/v). Sodium hydroxide (129 mg, 3.22 mmol) was added and the reaction mixture was stirred at 50° C. for 20 h. The resulting solution was acidified with 10% aqueous HCl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum to give 3-(2-(naphthalen-1-yl)acetamido)thiophene-2-carboxylic acid. Retention time=1.962 min, method [1], MS (ESI) 312.1 (M+H).

Workup

extractionextracted with ethyl acetate
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-0a0c47eba8524ae6b01ecee2941abd0f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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