Dichloromethane → 6-Chloronicotinic acid

HRID 637512Notes

Reaction equation

HRID 637512 reaction equation
CC(OC(C)=O)=O.[N+:8]1([O-])[C:9](=[CH:13][CH:14]=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17])C(O)=O.[OH-].[Na+].OC1C=CC(C(O)=O)=CN=1.C(Cl)[Cl:34]>CCN(CC)CC>[Cl:34][C:9]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:19][N:8]=1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 136435031-Oxo-1lambda~5~-pyridine-2,5-dicarboxylic acidHCID 178418479HCID 178418479, compound

Product 1

HCID 792226-Chloronicotinic acidYield 54.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

36.6 g of Ac2O, 60 g of Et3N and 600 g of CH2Cl2 were placed in a flask and heated at 40° C. 36.6 of isocinchomeronic acid-N-oxide was added in portions. After a further 1.5 hours, NaOH (10 percent) was added while strongly stirring until the final pH reached 13. The phases were separated. The CH2Cl2 -solution was dried with solid NaOH and was kept for the next batch. The aqueous solution was acidified with concentrated HCl (final pH was about 2). The product obtained hereby was sucked off, washed and dried. The yield was 54.2 percent of 2-chlor-5-pyridine carboxylic acid (6-chloronicotinic acid) and 37.7 percent of 2-hydroxy-5-pyridine carboxylic acid (6-hydroxynicotinic acid).

Workup

  1. customThe phases were separated
  2. dry with materialThe CH2Cl2 -solution was dried with solid NaOH
  3. customThe product obtained hereby
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-c2e60eb2a0b3428b81b7a3172d7af1d3
Source dataset
uspto-grants-1985_12
Patent number
US04556716

Reaction notes

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