Sodium Carbonate → HCID 19093694, compound

HRID 2254899Notes

Reaction equation

HRID 2254899 reaction equation
[C:1]([C:9]1[C:10]([CH3:28])=[N:11][C:12]([CH2:26][CH3:27])=[CH:13][C:14]=1[NH:15]S(C1C=CC(C)=CC=1)(=O)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[NH2:15][C:14]1[CH:13]=[C:12]([CH2:26][CH3:27])[N:11]=[C:10]([CH3:28])[C:9]=1[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 19093722HCID 19093722, compound

Product 1

HCID 19093694HCID 19093694, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of compound D (0.64 g) in concentrated sulphuric acid (3 ml) was heated at 50° C. for 1 hour. The solution was cooled to ambient temperature and added cautiously to crushed ice. The mixture was basified to pH 9 with solid sodium carbonate and the precipitate was collected by filtration to give 4-amino-3-benzoyl-6-ethyl-2-methylpyridine (B) (0.35 g) as a solid, m.p. 149°-151° C.; NMR (d6 -DMSO): 1.19(t, 3H), 1.97(s, 3H), 2.53(q, 2H), 5.78(s, 2H), 6.40(s, 1H), 7.49-7.73(m, 5H); mass spectrum (chemical ionisation, ammonia): 241(M+H)+.

Workup

  1. additionadded cautiously
  2. customto crushed ice
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-31108459ba6d4e18b92d3ea19285551f
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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