Methyl 2-formyl-6-nitrobenzoate → trans-3,4-Dihydro-2.2-dimethyl-4-(7-nitro-1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-ol

HRID 1656459Notes

Reaction equation

HRID 1656459 reaction equation
[NH2:1][C@@H:2]1[C:7]2[CH:8]=[C:9]([S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:20])([CH3:19])[C@H:3]1[OH:21].[CH:22]([C:24]1[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[C:25]=1[C:26](OC)=[O:27])=O.C([BH3-])#N.[Na+]>[Cl-].[Zn+2].[Cl-]>[CH3:20][C:4]1([CH3:19])[C@@H:3]([OH:21])[C@H:2]([N:1]2[CH2:22][C:24]3[C:25](=[C:30]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:32][CH:33]=3)[C:26]2=[O:27])[C:7]2[CH:8]=[C:9]([S:12]([C:15]([F:17])([F:18])[F:16])(=[O:14])=[O:13])[CH:10]=[CH:11][C:6]=2[O:5]1

Participants

5

Reactant 3

HCID 346007Methyl 2-formyl-6-nitrobenzoateHCID 5003444Sodium cyanoborohydrideHCID 15036014trans-4-amino-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl 2H-1-benzopyran-3-ol

Product 1

HCID 67902724trans-3,4-Dihydro-2.2-dimethyl-4-(7-nitro-1-oxoisoindolin-2-yl)-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-olYield 80.2%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Following the procedure and working up described in Example 10, but using 0.326 g of trans-4-amino-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-ol (prepared from its hydrochloride, in turn prepared as described in Preparation 9), 0.224 g of methyl 2-formyl-6-nitrobenzoate, 0.164 g of zinc chloride and 0.075 g of sodium cyanoborohydride, 0.391 g of the title compound, melting at 283°-284° C., were obtained.

Sources & evidence

ORD record
ord-0b5b3c6b99a34271872cc204ec4f23a1
Source dataset
uspto-grants-1993_10
Patent number
US05254578

Reaction notes

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