2-Chloroquinolin-6-ol → 4-(6-Hydroxyquinolin-2-yl)-3-methoxybenzoic acid

HRID 1627622Notes

Reaction equation

HRID 1627622 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=1[O:25][CH3:26])(O)O>>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=1[O:25][CH3:26])[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 221325772-Chloroquinolin-6-olHCID 231342764-Borono-3-methoxybenzoic acid

Product 1

HCID 569610574-(6-Hydroxyquinolin-2-yl)-3-methoxybenzoic acid

Procedure

Followed Scheme 3: Starting Materials: 2-chloroquinolin-6-ol and 4-borono-3-methoxybenzoic acid. 1H NMR (CD3OD, 400 MHz): δ 8.81 (d, J=8.4 Hz, 1H), 8.14 (d, J=9.2 Hz, 1H), 8.10 (d, J=8.4 Hz, 1H), 7.89 (dd, J=6.8, 1.6 Hz, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.69 (dd, J=9.2, 2.8 Hz, 1H), 7.48 (d, J=2.8 Hz, 1H). MS (ESI): m/z 295.7 [M+H]+.

Sources & evidence

ORD record
ord-f97c80aebd644bd1867f2c28f0e6f187
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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