Hydrochloric Acid → 1-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-pyridine-5-carboxylic acid

HRID 1752593Notes

Reaction equation

HRID 1752593 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:7]=[C:6]([C:20]([O:22]C)=[O:21])[C:5]=1[C:24]([O:26][CH3:27])=[O:25].O.Cl>CO>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[CH:7]=[C:6]([C:20]([OH:22])=[O:21])[C:5]([C:24]([O:26][CH3:27])=[O:25])=[C:4]([Cl:3])[C:9]2=[O:10])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 90447100Dimethyl 5-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridine-3,4-dicarboxylate

Product 1

HCID 904220291-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-pyridine-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium hydroxide (1.884 g, 44.8 mmol) was added to a solution of compound (9) (8.2 g, 22.42 mmol) in MeOH (150 ml)/water (100 ml). The reaction was stirred for about 12 h at r. t. and the reaction solution was adjusted to pH=2 with diluted aqueous HCl. The solid was filtered and washed with cold ether to give the title compound (8.4 g, 21.49 mmol, 96% yield). LC-MS (ESI+): m/e 352(M+H)+, Rt: 1.73 min; 1H-NMR (DMSO-d6, 400 MHz): δ=3.75 (s, 3H), 3.83 (s, 3H), 5.20 (s, 2H), 6.93 (d, 2H, J=8.8 Hz), 7.33 (d, 2H, J=8.8 Hz), 8.68 (s, 1H), 13.39 (br, 1H).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with cold ether

Sources & evidence

ORD record
ord-4134b9d8636c486b87d9dd4d74f37f5e
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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