p-Anisoyl chloride → Methyl 2-(4-methoxyphenyl)benzoxazole-4-carboxylate

HRID 506239Notes

Reaction equation

HRID 506239 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[NH2:12].[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=O)=[CH:17][CH:16]=1>>[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]2[O:1][C:2]3[C:3](=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][CH:11]=3)[N:12]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Product 1

HCID 14616764Methyl 2-(4-methoxyphenyl)benzoxazole-4-carboxylateYield 18%

Procedure

Methyl 2-(4-methoxyphenyl)benzoxazole-4-carboxylate was prepared from methyl 3-hydroxyanthranilate and 4-methoxybenzoyl chloride as described in Step A of Example 1. The product was obtained as an off-white solid in 18% yield. δ 8.29 (m, 2H), 8.01 (dd, J=7.8, 1.0 Hz, 1H), 7.74 (dd, J=8.1, 1.0 Hz, 1H), 7.37 (t, J=7.9 Hz, 1H), 7.03 (m, 2H), 4.06 (s, 3H); 3.91 (s, 3H); MS (ESI) m/z 284 [M+H]+.

Workup

  1. customThe product was obtained as an off-white solid in 18% yield

Sources & evidence

ORD record
ord-6a081441e42d42778a66eaedd6dcca60
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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