Sodium Hydroxide → HCID 178440410, compound

HRID 396131Notes

Reaction equation

HRID 396131 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9](=O)[CH:10]([CH3:12])[CH3:11].[N:14]([O-])=O.[Na+].O.O.[Sn](Cl)Cl.[OH-].[Na+]>O.Cl>[OH:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][N:14]=[C:9]2[CH:10]([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 230030871-(2-Amino-5-hydroxyphenyl)-2-methyl-1-propanoneHCID 23668193Sodium Nitrite

Product 1

HCID 178440410HCID 178440410, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of 900 mg (5.02 mmol) of 1-(2-amino-5-hydroxyphenyl)-2-methyl-1-propanone in 30 ml of half-conc. hydrochloric acid is treated slowly at −5° C. with a solution of 364 mg (5.27 mmol) of sodium nitrite in 15 ml of water and, after addition is complete, stirred at this temperature for 30 min. A solution of 2.266 g (10.04 mmol) of tin(II) chloride dihydrate in 15 ml of conc. hydrochloric acid is then added dropwise to the reaction mixture at −5° C. and the reaction is slowly warmed to room temperature. The mixture is neutralized using 45% strength sodium hydroxide solution, filtered off through kieselguhr, washed with ethyl acetate, and the organic phase is dried over sodium sulphate, concentrated in vacuo and dried. 370 mg (36%) of 5-hydroxy-3-isopropyl-1H-indazole are obtained.

Workup

  1. additionafter addition
  2. filtrationfiltered off through kieselguhr
  3. washwashed with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-ad11303350664a7a83e5caa8be24c66a
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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