Acrylamide → 3-[2-Methyl-3-keto-1,4-benzoxazin-6-yl]-acrylamide

HRID 840370Notes

Reaction equation

HRID 840370 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.[C:14]([NH2:18])(=[O:17])[CH:15]=[CH2:16].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][CH:9]1[C:8](=[O:12])[NH:7][C:6]2[CH:13]=[C:2]([CH:16]=[CH:15][C:14]([NH2:18])=[O:17])[CH:3]=[CH:4][C:5]=2[O:10]1

Participants

7

Reactant 3

HCID 6579AcrylamideHCID 80271Tri-o-tolylphosphineHCID 226229036-bromo-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 537199093-[2-Methyl-3-keto-1,4-benzoxazin-6-yl]-acrylamideYield 36%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

726 mg of 6-bromo-2-methyl-1,4-benzoxazin-3-(4H)-one is stirred in 1.5 ml of triethylamine with 0.267 g of acrylamide as well as 8 mg of palladium(II) acetate and 46 mg of tri-ortho-toluyl-phosphine for several hours at 100° C. The product is taken up in methanol and purified by column chromatography with an ethanol/ethyl acetate mixture. Yield 36%.

Workup

  1. custompurified by column chromatography with an ethanol/ethyl acetate mixture

Sources & evidence

ORD record
ord-6ee9fa08e43447fab01785277a1263a0
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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