Methane → HCID 504661, compound

HRID 2351275Notes

Reaction equation

HRID 2351275 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]([O:15][CH2:16][CH3:17])=O.C>N1C=CC=CC=1.CCOCC>[CH2:16]([O:15][C:13]1[O:5][C:4](=[O:6])[C:3]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:2]=2[N:1]=1)[CH3:17]

Participants

6

Reactant 3

HCID 297MethaneHCID 10928Ethyl chloroformateHCID 1512106-Methylanthranilic acid

Product 1

HCID 504661HCID 504661, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-amino-6-methyl benzoic acid (25g., 0.165 mol) in dry pyridine (125 ml) at room temperature under anhydrous conditions was added ethyl chloroformate (47.33 ml, 3 equiv.) in a dropwise manner over 15 minutes. After stirring for 2 hours, the excess pyridine was removed under reduced pressure at a bath temperature of 40° C., and the residue was stirred vigorously in ice-cold water (250 ml) for 15 minutes. The pale yellow powder was collected by filtration, washed with water (100 ml) and air-dried to give the crude product (30.4g). The crude product was treated with active charcoal (2g) in ether (200ml) to afford a white solid after removal of solvent. Recrystallization from EtOAc/pet. ether gave 2-ethoxy-5-methyl-4H-3,1-benzoxazin-4-one (28.1g, 83%) as colorless crystals; m.p. 104°-105° C.; analysis for C11H11NO3 : C, 64.38; H, 5.40; N, 6.83. Found: C, 64.21; H, 5.43; N, 6.80.

Workup

  1. customthe excess pyridine was removed under reduced pressure at a bath temperature of 40° C.
  2. stirringthe residue was stirred vigorously in ice-cold water (250 ml) for 15 minutes
  3. filtrationThe pale yellow powder was collected by filtration
  4. washwashed with water (100 ml)
  5. customair-dried
  6. customto give the crude product (30.4g)
  7. customto afford a white solid
  8. customafter removal of solvent
  9. customRecrystallization from EtOAc/pet. ether

Sources & evidence

ORD record
ord-e88efd4c5dc24b789e600584790dc21f
Source dataset
uspto-grants-1989_10
Patent number
US04873232

Reaction notes

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