Tetrahydrofuran → 2-Oxo-1,2,4a,8a-tetrahydroquinoline-6-carboxylic Acid

HRID 509341Notes

Reaction equation

HRID 509341 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([O:14]C)=[O:13])[CH:8]=2)[N:3]=1.C1C[O:19]CC1>>[O:19]=[C:2]1[CH:11]=[CH:10][CH:9]2[CH:4]([CH:5]=[CH:6][C:7]([C:12]([OH:14])=[O:13])=[CH:8]2)[NH:3]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 56924381Methyl 2-chloroquinoline-6-carboxylate

Product 1

HCID 866879572-Oxo-1,2,4a,8a-tetrahydroquinoline-6-carboxylic Acid

Procedure

A solution of methyl 2-chloroquinoline-6-carboxylate (60 mg, 0.271 mmol) in THF/5 N aqueous HCl (1:1, 2 mL) was heated to 60° C. in a heating block. LCMS shows major product 86% peak area corresponding to title compound with hydrolysis of methyl ester (m/z=189.9). The reaction was concentrated and used in the subsequent amide coupling steps without further purification.

Sources & evidence

ORD record
ord-a07ea94a92a346e2945d3fde79b1e7f5
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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