Hydrochloric Acid → 6-methoxy-N-methyl-4-o-tolylpyridin-3-amine

HRID 877973Notes

Reaction equation

HRID 877973 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:3]=1.[OH-:17].[Na+].Cl.[CH3:20]O>>[CH3:20][O:17][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 577104436-chloro-N-methyl-4-(2-methylphenyl)pyridin-3-amine

Product 1

HCID 706633806-methoxy-N-methyl-4-o-tolylpyridin-3-amine

Procedure

6-Chloro-N-methyl-4-o-tolylpyridin-3-amine (150 mg, 0.645 mmol, prepared as described in WO2005/002577) in a 10% NaOH solution in CH3OH (300 mg NaOH in 3 mL CH3OH) was heated to 160° C. for 3 hours. After cooling, the reaction mixture was neutralized with 6M aqueous HCl and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. Filtration followed by removal of volatiles in vacuo gave a gummy oil. The desired compound was isolated by flash chromatography on silica gel (20% EtOAc in n-hexane) as a white waxy solid (115 mg, 78%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration
  6. customfollowed by removal of volatiles in vacuo
  7. customgave a gummy oil

Sources & evidence

ORD record
ord-8b751125510c441eadbd0068c3184e1f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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