Hydrochloric Acid → 2-Chloro-6-methylpyrimidine-4-carboxylic acid

HRID 2069381Notes

Reaction equation

HRID 2069381 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([Cl:12])[N:6]=1)=[O:4].[OH-].[Na+].Cl>C(#N)C>[Cl:12][C:7]1[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[C:9]([CH3:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylate

Product 1

HCID 105352132-Chloro-6-methylpyrimidine-4-carboxylic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of commercially available methyl-2-chloro-6-methylpyrimidine-4-carboxylate (6.00 g, 32.15 mmol) in acetonitrile (500 mL), 1M aq. solution of NaOH (48.2 mL) is added at 0° C. The mixture is stirred at 0° C. for 1 h then acidified with 25% aq. HCl (7 mL). Volatiles are evaporated and the aq. solution is extracted with ethylacetate, washed with brine, dried over Na2SO4, filtered and concentrated to give 2-chloro-6-methylpyrimidine-4-carboxylic acid (4.22 g) as a yellow crystalline solid; LC-MS: tR=0.42 min, [M+H]+=172.96; 1H NMR (D6-DMSO): δ 2.58 (s, 3H), 7.95 (s, 1H), 14.1 (s br, 1H).

Workup

  1. customVolatiles are evaporated
  2. extractionthe aq. solution is extracted with ethylacetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15eaeda0d354494e91fe8b04ccdccdf4
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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