Dichloromethane → (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

HRID 633960Notes

Reaction equation

[OH-].[Na+].CN1CC[C:7]2([CH2:18][C:17]3[C:12](=[N:13][CH:14]=[C:15](/[CH:19]=[CH:20]/[C:21]([O:23]CC)=[O:22])[CH:16]=3)[NH:11][C:10]2=[O:26])CC1.[Cl:27]CCl>C(O)C>[ClH:27].[O:26]=[C:10]1[NH:11][C:12]2[N:13]=[CH:14][C:15](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[CH:16][C:17]=2[CH2:18][CH2:7]1

Participants

Conditions

Temperature: 45 °C

Procedure

An aqueous solution of sodium hydroxide (1N, 7.83 mL) was added to a solution of (E)-ethyl 3-(1′-methyl-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (860 mg, 2.61 mmol) in a mixture of dichloromethane (10 mL) and ethanol (10 mL) at room temperature. The reaction mixture was stirred at 45° C. overnight then concentrated to dryness. The residue was acidified by addition of an aqueous solution of hydrochloric acid (1N, 30 mL) until pH 1. The resulting solid was filtered and washed with water and diethyl ether. The title product was obtained as a white solid (586 mg, 66%).

Workup

concentrationthen concentrated to dryness
additionThe residue was acidified by addition of an aqueous solution of hydrochloric acid (1N, 30 mL) until pH 1
filtrationThe resulting solid was filtered
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-ab0fd4c108c04deeb7755bd23dcd823b
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321769B2

Reaction notes

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