Hydrochloric Acid → HCID 21074240, compound

HRID 1373175Notes

Reaction equation

HRID 1373175 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[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.O.C(OCC)(=O)C.C(O)(=O)C>[OH:4][C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[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

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 21074238HCID 21074238, compound

Product 1

HCID 21074240HCID 21074240, compoundYield 91.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-{[3-acetoxy-5-(2-methylbenzyloxy)benzoyl]amino}-3-pyridinecarboxylate (11.64 g, 26.8 mM) was dissolved in THF (150 ml) and sodium methoxide (25% in methanol) (11.6 ml, 53.6 mM) was added. The resulting yellow solution was stirred for 20 minutes at ambient temperature and was then added to dilute hydrochloric acid. The pH of the mixture was adjusted to pH=4 by the addition of sodium bicarbonate and acetic acid before ethyl acetate (50 ml) and water (25 ml) were added. This resulted in the precipitation of a colourless solid which was isolated by filtration and washed with water and ethyl acetate before being dried over magnesium sulphate, filtered, to give methyl 6-{[3-hydroxy-5-(2-methylbenzyloxy)benzoyl]amino}-3-pyridinecarboxylate as a colourless solid (9.62 g); H1 NMR δ (d6-DMSO) 2.33 (3H s) 3.85 (3H s) 5.11 (2H s) 6.61 (1H s) 7.01 (1H s) 7.18–7.29 (4H m) 7.40 (1H d) 8.32 (2H s) 8.90 (1H s) 9.77 (1H s) 11.04 (1H s).

Workup

  1. additionwere added
  2. customThis resulted in the precipitation of a colourless solid which
  3. customwas isolated by filtration
  4. washwashed with water and ethyl acetate
  5. dry with materialbefore being dried over magnesium sulphate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ebd169c926cb4ff68ce89ca13a4bf583
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

Loading…