Water → 6-Methyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1295194Notes

Reaction equation

HRID 1295194 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C(=O)(O)[O-].[Na+].O.Cl[CH2:17][C:18](Cl)=[O:19]>CC(=O)CC>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][CH2:17][C:18](=[O:19])[NH:1][C:2]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 885002-Amino-6-methylpyridin-3-olHCID 516892Sodium Bicarbonate

Product 1

HCID 218737086-Methyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a suspension of 2-amino-6-methyl-pyridin-3-ol (18.3 g, 148 mmol), sodium bicarbonate (30 g, 354 mmol), H2O (100 mL), and 2-butanone (100 mL) in an ice-water bath was added a solution of chloroacetyl chloride (13.3 mL. 167 mmol) in 2-butanone (30 mL) over 1.5 h, controlling the temperature below 10 ° C. After the addition was complete, the ice-water bath was removed and the mixture was stirred at ambient temperature for 30 minutes, followed by refluxing for 1.5 h. The solvents were evaporated, and the resulting solid was washed with H2O (3 times), and dried under high vacuum overnight, giving the title compound (19.2 g, 79% yield) as a pale yellow solid. 1H NMR (CDCl3) δ 10.45 (bs, 1H), 7.17 (d, 1H, J=8.1 Hz), 6.78 (d, 1H, J=8.1 Hz), 4.62 (s, 2H), 2.52 (s, 3H). Mass spectrum (LCMS, ESI) calculated for C8H9N2O2 165.1 (M+1); found 165.1.

Workup

  1. customthe temperature below 10 ° C
  2. additionAfter the addition
  3. customthe ice-water bath was removed
  4. temperatureby refluxing for 1.5 h
  5. customThe solvents were evaporated
  6. washthe resulting solid was washed with H2O (3 times)
  7. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-1c7fb303a8db4938a79c7f742f39155c
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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