5-Methoxy-3-methyl-phthalic anhydride → 6-Methoxy-4-methyl-isoindole

HRID 41474Notes

Reaction equation

HRID 41474 reaction equation
COC1C=C2C(OC(=O)C2=C(C)C=1)=O.[CH3:15][O:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21](=O)[NH:22][C:23]2=O)=[C:19]([CH3:28])[CH:18]=1>>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH3:28])[C:20]2[C:24]([CH:25]=1)=[CH:23][NH:22][CH:21]=2

Participants

3

Reactant 2

HCID 2839025-Methoxy-3-methyl-phthalic anhydrideHCID 666723406-Methoxy-4-methyl-isoindole-1,3-dione2×

Product 1

HCID 666724646-Methoxy-4-methyl-isoindole

Procedure

5-Methoxy-3-methyl-phthalic anhydride was used to prepare 6-methoxy-4-methyl-isoindole-1,3-dione. 1H NMR (DMSO-d6) 11.05 (1H, br.s), 7.13 (1H, d), 7.10 (1H, d), 3.88 (3H, s), 2.55 (3H, s). Reduction of 6-methoxy-4-methyl-isoindole-1,3-dione according to the method of preparation C2 afforded 6-methoxy-4-methyl-isoindole. 1H NMR (DMSO-d6) 6.64 (1H, s), 6.57 (1H, s), 4.05 (2H, s), 3.96 (2H, s), 3.70 (3H, s), 2.16 (3H, s). MS: [M+H]+ 164.

Sources & evidence

ORD record
ord-d929e57795314214ae939f40abb6a27c
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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