Hydrochloric Acid → 6-[(3-Isobutoxy-5-isopropoxybenzoyl)amino]nicotinic acid

HRID 1373177Notes

Reaction equation

HRID 1373177 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[CH:24]=1)[C:9]([NH:11][C:12]1[N:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=1)=[O:10])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].O.Cl>C1COCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:22]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[CH:24]=1)[C:9]([NH:11][C:12]1[N:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1)=[O:10])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21074242Methyl 6-[(3-isobutoxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate

Product 1

HCID 100447926-[(3-Isobutoxy-5-isopropoxybenzoyl)amino]nicotinic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[(3-isobutoxy-5-isopropoxybenzoyl)amino]-3-pyridinecarboxylate (230 mg, 0.62 mM) was dissolved in THF (8 ml) and a 2M NaOH solution (1.2 ml, 2.40 mM) was added. Water (7 ml) was added to the reaction mixture until it became monophasic. The reaction was stirred for 6 hours at ambient temperature and was then acidified to pH=1 with 1N aqueous HCl. The white solid which precipitated from the mixture was isolated by filtration and dried to give the title compound as a colourless solid (195 mg); H1 NMR δ (d6-DMSO) 0.99 (6H d) 1.12 (6H d) 2.00 (1H sept) 3.80 (2H d) 4.65 (1H sept) 6.62 (1H s) 7.19 (2H s) 8.30 (2H s) 8.86 (1H s) 11.09 (1H s br); [M+H]373; [M−H] 371.

Workup

  1. customThe white solid which precipitated from the mixture
  2. customwas isolated by filtration
  3. customdried

Sources & evidence

ORD record
ord-111fb553c42a4dbaa354f4fb0b54fc7c
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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