Methyl iodide → 4-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-4H-benzo[1,4]oxazin-3-one

HRID 2386777Notes

Reaction equation

HRID 2386777 reaction equation
[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:14](=[O:25])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[Cl:24])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:26])[CH:2]=[CH2:3].[CH3:27]I>C(O)C>[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:14](=[O:25])[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[Cl:24])[CH3:27])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:26])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 666972884-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-acetyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 666972384-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In analogy to Example 56, step 2, 4-allyl-6-[2-(2-chloro-4-methoxy-phenyl)-acetyl]-4H-benzo[1,4]oxazin-3-one (8.9 g) was reacted with methyl iodide at r.t. for 2 h. The crude product was treated with ethanol (25 ml), filtered and dried under high vacuum to give the title compound (7.2 g) as a light yellow solid. MS (m/e)=386.2 [M+H+].

Workup

  1. filtrationfiltered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-e9eba2c50e0940458b6c75e1385a9cf7
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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