Methanol → 2H-1,2-Benzoxazin-3(4H)-one

HRID 1699979Notes

Reaction equation

HRID 1699979 reaction equation
[C:1]([NH2:7])(=[O:6])[C:2](C)(C)C.Cl[C:9]1[CH:15]=[CH:14][C:12](N)=[CH:11][CH:10]=1.C([Li])CCC.C[OH:22]>>[O:22]1[C:10]2[CH:11]=[CH:12][CH:14]=[CH:15][C:9]=2[CH2:2][C:1](=[O:6])[NH:7]1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 78124-ChloroanilineHCID 12957TrimethylacetamideHCID 178418339Butyllithium

Product 1

HCID 199374482H-1,2-Benzoxazin-3(4H)-one

Procedure

This general method teaches (1) metallation of the pivalamide of parachloroaniline with n-butyllithium followed by nucleophilic substitution with an ester to form a ketone, (2) synthesis of a tertiary carbinol by Grignard addition to the ketone, and (3) cyclization of the unprotected amine with the carbinol by addition of a condensing agent to form a benzoxazinone.

Workup

  1. customto form
  2. additionby addition of a condensing agent

Sources & evidence

ORD record
ord-30e89d7f2e944a8fb5ce9258d2a39fa1
Source dataset
uspto-grants-2002_02
Patent number
US06348616B1

Reaction notes

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