2-Chloro-6-methoxyquinoline → 4-(6-Hydroxyquinolin-2-yl)benzoic acid

HRID 1507333Notes

Reaction equation

HRID 1507333 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[N:3]=1.C[O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17]>>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:21]1[CH:22]=[CH:23][C:18]([C:16]([OH:17])=[O:15])=[CH:19][CH:20]=1)[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 836472-Chloro-6-methoxyquinoline2×HCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 569607754-(6-Hydroxyquinolin-2-yl)benzoic acid

Procedure

Followed Scheme 2, A conditions: Starting materials: 2-chloro-6-methoxyquinoline (Intermediate 1) (100 mg, 0.52 mmol) and (4-(methoxycarbonyl)phenyl) boronic acid. 1H NMR (DMSO-d6, 400 MHz): δ 13.06-12.90 (bs, 1H), 10.14 (s, 1H), 8.36-8.33 (d, 2H), 8.30-8.27 (d, 1H), 8.11-8.06 (m, 3H), 7.97-7.94 (d, 1H), 7.38-7.34 (dd, 1H), 7.20 (s, 1H). MS (ESI): m/z 266.08 [M+H]+.

Sources & evidence

ORD record
ord-eaadf976bf844986a56a69cb9718c78f
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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