Hydrochloric Acid → HCID 21074235, compound

HRID 1373171Notes

Reaction equation

HRID 1373171 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([O:24]C(=O)C)[CH:23]=1)[C:8]([NH:10][C:11]1[N:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1)=[O:9])(=O)C.C[O-].[Na+].Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:4][C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([OH:24])[CH:23]=1)[C:8]([NH:10][C:11]1[N:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 21074233HCID 21074233, compound

Product 1

HCID 21074235HCID 21074235, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-[(3,5-di-acetoxybenzoyl)amino]-3-pyridinecarboxylate (6 g, 16.1 mM) was stirred at ambient temperature in THF (50 ml) and sodium methoxide solution (14.8 ml of 25% in methanol, 64.4 mM) added slowly. The resultant solution was stirred for one hour, poured into 1M hydrochloric acid and the pH adjusted to pH=4 with sodium bicarbonate solution, extracted with ethyl acetate, extracts combined, washed with brine and dried over anhydrous magnesium sulphate. The solvent was removed by distillation under reduced pressure to give a yellow solid. This solid was triturated with hot methanol, filtered, to give methyl 6-[(3,5-dihydroxybenzoyl)amino]-3-pyridinecarboxylate as a pale yellow solid (3.51 g, 77%); H1 NMR δ (d6-DMSO) 3.85 (3H s) 6.41 (1H s) 6.80 (2 H d)8.28 (2 Hm)8.85 (1 Hd)9.52 (2 H s)

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customto give a yellow solid
  6. customThis solid was triturated with hot methanol
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6b8137c8f66e411baabb3fd1a459f19b
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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