Hydrochloric Acid → 4-(3-Carbamoyl-6-chloropyridin-2-ylamino)benzoic acid

HRID 2044056Notes

Reaction equation

HRID 2044056 reaction equation
[C:1]([C:4]1[C:5]([NH:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)(=[O:3])[NH2:2].[OH-].[Na+].Cl>CO>[C:1]([C:4]1[C:5]([NH:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57489609Methyl 4-(3-carbamoyl-6-chloropyridin-2-ylamino)benzoate

Product 1

HCID 574896104-(3-Carbamoyl-6-chloropyridin-2-ylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(3-carbamoyl-6-chloropyridin-2-ylamino)benzoate was dissolved in 20 mL of MeOH, treated with 10 mL of 30% NaOH, and stirred at rt for 3 h. The reaction mixture was acidified with 1N HCl and the resulting solid was filtered and air dried to give 1.43 g of 4-(3-carbamoyl-6-chloropyridin-2-ylamino)benzoic acid as a yellow solid. LCMS: (M+H)+=292.06, 294.00 (Cl pattern).

Workup

  1. filtrationthe resulting solid was filtered
  2. customair dried

Sources & evidence

ORD record
ord-00b01ce3bd1d417d853c8ba16ec31ba4
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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