4-Chlorophthalic anhydride → 4-(5-Chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

HRID 1175040Notes

Reaction equation

HRID 1175040 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[O:5][C:4]([CH3:15])([CH3:14])[C@H:3]1[OH:16].[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=O)[O:22][C:21]2=[O:28]>>[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:22])[N:1]([CH:2]1[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=3)[O:5][C:4]([CH3:14])([CH3:15])[CH:3]1[OH:16])[C:21]2=[O:28]

Participants

3

Reactant 2

HCID 670444-Chlorophthalic anhydrideHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 667000584-(5-Chloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Procedure

Following the procedure in Example 89, using (3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile and 5-chloro-isobenzofuran-1,3-dione as starting materials, the title compound was prepared as a pale yellow solid.

Sources & evidence

ORD record
ord-1b6140e5ce8c4ae4944f9c059636512d
Source dataset
uspto-grants-2010_11
Patent number
US07838553B2

Reaction notes

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