Stannous chloride dihydrate → HCID 178441966, compound

HRID 396132Notes

Reaction equation

HRID 396132 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH:11]([CH3:13])[CH3:12].[N:15]([O-])=O.[Na+].O.O.[Sn](Cl)Cl>O.Cl>[OH:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][N:15]=[C:9]2[CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 230030541-(2-Amino-5-hydroxyphenyl)-3-methyl-1-butanoneHCID 23668193Sodium Nitrite

Product 1

HCID 178441966HCID 178441966, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

In an analogous manner to the procedure of Example XIV, 783 mg (4.05 mmol) of 1-(2-amino-5-hydroxyphenyl)-3-methyl-1-butanone in 30 ml of half-conc. hydrochloric acid are reacted with 294 mg (4.25 mmol) of sodium nitrite in 15 ml of water and 914 mg (4.05 mmol) of tin(II) chloride dihydrate in 15 ml of conc. hydrochloric acid to give 317 mg (41%) of 5-hydroxy-3-isobutyl-1H-indazole.

Sources & evidence

ORD record
ord-ac4c4b51e7d34aea93cc5e2f5f6ecc78
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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