Hydrochloric Acid → HCID 14424003, compound

HRID 621413Notes

Reaction equation

HRID 621413 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12](=[O:22])[NH:11][C:10]=2[CH:23]=1.[ClH:24].[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27]>O.[Cu]=O.CC(C)=O>[CH2:15]([CH:13]1[C:12](=[O:22])[NH:11][C:10]2[CH:23]=[C:6]([CH2:27][CH:26]([Cl:24])[C:25]([O:29][CH3:30])=[O:28])[CH:7]=[CH:8][C:9]=2[O:14]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 14423999HCID 14423999, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14424003HCID 14424003, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of 1.3 g of sodium nitrite in 3 ml of water is added to a mixture of 4.8 g of 6-amino-2-benzyl-3-oxo-1,4-benzoxazine, 3 ml of conc. hydrochloric acid and 60 ml of acetone. After the mixture is stirred at room temperature for 30 minutes, 10.6 ml of methyl acrylate are added thereto, and 500 mg of copper oxide (I) are added gradually at a temperature of 35° to 40° C. After stirring for 30 minutes, the mixture is poured into water and extracted with ethyl acetate. The extract is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=100:1) to give 4.95 g of crude methyl 3-(2-benzyl-3-oxo-1,4-benzoxazin-6-yl)-2-chloropropionate.

Workup

  1. stirringAfter stirring for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-6a83f8756a2b468292b0a94d99e6de32
Source dataset
uspto-grants-1989_04
Patent number
US04824833

Reaction notes

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