Hydrochloric Acid → 3,4-Dichloro-2-methylpyridine

HRID 1655206Notes

Reaction equation

HRID 1655206 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]=1[Cl:13].[OH-].[Na+].[ClH:16]>>[Cl:13][C:7]1[C:8]([CH3:12])=[N:9][CH:10]=[CH:11][C:6]=1[Cl:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 134195733-Chloro-2-methylpyridin-4-amineHCID 23668193Sodium Nitrite

Product 1

HCID 219228903,4-Dichloro-2-methylpyridine

Procedure

Sodium nitrite (36 g) was added in portions to a stirred solution of 4 -amino-3 -chloro-2 -picoline (24.85 g) in conc. hydrochloric acid (750 ml) cooled to 0°-5°. After 1 hour at 0°-5 ° and a further 2 hours at room temperature the mixture was basified (NaOH), allowing the temperature to rise to ca. 50°, and extracted with ether. After drying (K2CO3 ), the extract was evaporated to dryness to give 3,4 -dichloro-2 -picoline (26.5 g) as a low melting solid.

Workup

  1. temperaturecooled to 0°-5°
  2. customa further 2 hours
  3. customat room temperature
  4. customto rise to ca. 50°
  5. extractionextracted with ether
  6. dry with materialAfter drying (K2CO3 )
  7. customthe extract was evaporated to dryness

Sources & evidence

ORD record
ord-1add5da34bca442e9efa57a72c02633c
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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