Pyridine → HCID 20208336, compound

HRID 542495Notes

Reaction equation

HRID 542495 reaction equation
[CH3:1][NH:2][C:3]1[O:8][C:7](=[O:9])[C:6]2[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]=1.C(OC(=O)C)(=[O:17])C.N1[CH:27]=[CH:26]C=CC=1.CN(C1C=CC=CN=1)C>O1CCCC1>[CH3:26][CH2:27][C:1]([NH:2][C:3]1[O:8][C:7](=[O:9])[C:6]2[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:5]=2[N:4]=1)=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 13221326HCID 13221326, compound

Product 1

HCID 20208336HCID 20208336, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 mg 2-methylamino-5-methyl-4H-3,1-benzoxazin-4-one, prepared as described in Example I, above, in 20 ml of dry tetrahydrofuran, was added 3 ml of acetic anhydride, 3 ml of pyridine and 25 mg of dimethylaminopyridine. The solution was stirred at room temperature for 3 days. The solvent was removed under reduced pressure, and remaining trace amounts of acetic anhydride and pyridine were removed by azeotroping with toluene. The residue was purified by column chromatography over silica gel (10% ethyl acetate:petroleum ether, 30°-60° C.) to yield 210 mg of 2-(N-methylacetylamino)-5-methyl-4H-3,1-benzoxazin-4-one, m.p. 108°-109° C., 'H NMR: (delta CDCl3); 2.6 (s, 3H, CH3 -Ar), 2.8 (s, 3H, CH3), 3.4 (s, 3H, NMe), 7.1-7.8 (m, 3H, Ar-H); IR: 1765, 1690, 1640, 1620, 1600 cm-1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customwere removed
  3. customby azeotroping with toluene
  4. customThe residue was purified by column chromatography over silica gel (10% ethyl acetate:petroleum ether, 30°-60° C.)

Sources & evidence

ORD record
ord-87c683156dd34461bf4a66184222df36
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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