Hydrochloric Acid → 4-(Aminocarbonyl)-3-(cyclopentylamino)-benzoic acid

HRID 906145Notes

Reaction equation

[NH2:1][C:2]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][C:5]=1[NH:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:3].[OH-].[K+].Cl>CO.O>[NH2:1][C:2]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[NH:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:3]

Participants

Conditions

Temperature: 55 °C

Procedure

A suspension of ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)-benzoate (333 mg, 1.21 mmol) and potassium hydroxide (135 mg, 2.41 mmol) in methanol (6 mL) and water (2 mL) was stirred at 55° C. for 1 h. After cooling to room temperature, water was added and the pH adjusted to 4 with 1N aqueous hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and dried to provide 4-(aminocarbonyl)-3-(cyclopentylamino) benzoic acid (260 mg, 87% yield). 1H NMR (400 MHz, DMSO-d6): 13.02 (br s, 1H), 8.17 (d, 1H), 7.97 (br s, 1H), 7.66 (d, 1H), 7.34 (br s, 1H), 7.21 (d, 1H), 7.04 (dd, 1H), 3.81 (m, 1H), 1.99 (m, 2H), 1.64 (m, 4H), 1.42 (m, 2H). MS (EI) for C13H16N2O3: 249 (MH+).

Workup

temperatureAfter cooling to room temperature
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-881d0c37bb8e4360ab70fbbf7297e4b5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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