Hydrochloric Acid → 6-Chloro-5-methoxynicotinic acid

HRID 1924852Notes

Reaction equation

HRID 1924852 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Cl:12])=[N:6][CH:5]=1.[OH-].[Na+].Cl>CO>[Cl:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:4]([C:3]([OH:13])=[O:2])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57336616Methyl 6-chloro-5-methoxynicotinate

Product 1

HCID 469118426-Chloro-5-methoxynicotinic acidYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-chloro-5-methoxynicotinic acid methyl ester (1.3 g, 6.4 mmol) in MeOH (4 mL) at 25° C. was added 10% NaOH aqueous solution (19.3 mmol). The reaction was stirred for 24 h, then placed into an ice water bath and acidified with 2M HCl until pH=2 was achieved. The flask was then placed into a refrigerator for 3 h. The white precipitate was filtered off and rinsed with cold H2O. The solid was dissolved in acetone, dried over MgSO4 and concentrated to furnish the product 6-chloro-5-methoxynicotinic acid as a yellow solid (0.895 g, 74%); 1H NMR (400 MHz, CDCl3) δ 8.45 (d, 1H), 7.66 (d, 1H), 3.83 (s, 3H).

Workup

  1. customplaced into an ice water bath
  2. waitThe flask was then placed into a refrigerator for 3 h
  3. filtrationThe white precipitate was filtered off
  4. washrinsed with cold H2O
  5. dissolutionThe solid was dissolved in acetone
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3e17597540444720aed008e94c68e7e4
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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