Stannous chloride dihydrate → 4-(4-Amino-2-fluorophenoxy)-1,2-benzisoxazole-3-amine

HRID 16398Notes

Reaction equation

[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:10]2[C:11]([NH2:14])=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:19][C:17]1[CH:16]=[CH:15][C:3]([O:4][C:5]2[C:10]3[C:11]([NH2:14])=[N:12][O:13][C:9]=3[CH:8]=[CH:7][CH:6]=2)=[C:2]([F:1])[CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

120 mg (0.41 mmol) of 4-(2-fluoro-4-nitrophenoxy)-1,2-benzisoxazole-3-amine (from example VI) and 468 mg (2.07 mmol) of tin(II) chloride dihydrate are dissolved in 8 ml of ethyl acetate and heated at 70° C. for 4 hours. After cooling to room temperature, the reaction solution is adjusted to pH 9 using saturated sodium bicarbonate solution, which gives a colorless precipitate. 5 g of kieselguhr are added to the suspension, and the mixture is filtered. The filtrate is extracted repeatedly with ethyl acetate. The combined organic phases are washed with water and dried over sodium sulfate. Removal of the solvent under reduced pressure gives the product.

Workup

temperatureAfter cooling to room temperature
customgives a colorless precipitate
addition5 g of kieselguhr are added to the suspension
filtrationthe mixture is filtered
extractionThe filtrate is extracted repeatedly with ethyl acetate
washThe combined organic phases are washed with water
dry with materialdried over sodium sulfate
customRemoval of the solvent under reduced pressure
customgives the product

Sources & evidence

ORD record: ord-68b7d0d38e8343dab3fe45c8f977cab9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737153B2

Reaction notes

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