Hydrochloric Acid → 6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid hydrochloride

Reaction equation

C([O:3][C:4]([C:6]1(C(OCC)=O)[CH2:14][C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7]1)=[O:5])C.[ClH:20]>>[ClH:20].[N:12]1[C:13]2[CH2:14][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 21260369Diethyl 5H-Cyclopenta[b]pyridine-6,6(7H)-dicarboxylate

Product 1

HCID 685628996,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid hydrochloride

Procedure

5,7-Dihydro-[1]pyrindine-6,6-dicarboxylic acid diethyl ester (0.953 g, 3.62 mmol) is taken into concentrated hydrochloric acid, heated to reflux for 4 hours and evaporated to afford 6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid hydrochloride. δc (DMSO-d6) 33.9 (t), 34.5 (t) 41.2 (d), 124.8 (d), 140.1 (d), 140.8 (d), 141.2 (s), 158.4 (s), 175.2 (s).

Workup

temperatureheated
temperatureto reflux for 4 hours
customevaporated

Sources & evidence

ORD record: ord-d044b15e3bc640e38db51ed53b337563
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745462B2

Reaction notes

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