Stannous Chloride → 5-benzenesulfonyl-1H-indazol-3-ylamine

HRID 1640967Notes

Reaction equation

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

Participants

Conditions

Temperature: 4 °C

Procedure

2-Amino-5-benzenesulfonyl-benzonitrile (0.81 g, 3.15 mmol) in 37% HCl (5 mL) was treated dropwise at 4° C. with NaNO2 (261 mg, 3.78 mmol) in 5 mL of water. After 1.75 hours the suspension was added dropwise to a solution of SnCl2 (4.88 g, 25.21 mmol) in 5 mL of 37% HCl. After stirring at 4° C. for 3 hours the solid was filtered, taken up with water (30 mL) and boiled for 1.5 hours. The hot mixture was filtered and washed thoroughly with boiling water. The filtrate was cooled to 4° C. and treated under stirring with 17% NaOH (approximately 5 mL) dropwise. After overnight cooling in a fridge the solid was filtered and washed with water to neutral pH affording 0.348 g of title compound (40% yield).

Workup

filtrationwas filtered
waitboiled for 1.5 hours
filtrationThe hot mixture was filtered
washwashed thoroughly with boiling water
temperatureThe filtrate was cooled to 4° C.
additiontreated
stirringunder stirring with 17% NaOH (approximately 5 mL) dropwise
temperatureAfter overnight cooling in a fridge the solid
filtrationwas filtered
washwashed with water to neutral pH

Sources & evidence

ORD record: ord-059d09c348014e7cb318c08f3617d40c
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114865B2

Reaction notes

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