Sodium Carbonate → 4,5-Dimethylpyridin-2-amine

HRID 869889Notes

Reaction equation

HRID 869889 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([N:9]2C(=O)C3C=CC=CC=3OC2(C)C)[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 687366023-(4,5-Dimethylpyridin-2-yl)-2,2-dimethyl-2h-benzo[e][1,3]oxazin-4(3h)-one

Product 1

HCID 124040134,5-Dimethylpyridin-2-amineYield 103.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-(4,5-dimethylpyridin-2-yl)-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4(3H)-one (9 g, 0.03 mol) in concentrated hydrochloric acid (100 mL) was heated at reflux overnight. The mixture was basified by saturated solution of Na2CO3 and extracted with CH2Cl2 (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give 4,5-dimethylpyridin-2-amine (3.8 g, 97%), that was directly used in the next step without further purification.

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with CH2Cl2 (100 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-98f05b2c33c34d7d99ffa5c83fa8657f
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

Loading…