Acetic Acid → HCID 23048269, compound

HRID 2107347Notes

Reaction equation

HRID 2107347 reaction equation
[NH2:1](=S)[NH2:2].[C:4]([OH:7])(=O)[CH3:5].[C:8]1(C)[CH:13]=[CH:12]C=[CH:10][CH:9]=1>C1(C)C(C)=CC=CC=1>[NH:1]1[C:10]2[CH:5]([CH2:12][CH2:13][CH2:8][CH:9]=2)[C:4](=[O:7])[NH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1140TolueneHCID 129772811HCID 129772811, compound

Product 1

HCID 23048269HCID 23048269, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The aminosulfide (IV) is then reacted with conc. hydrochloric acid at a temperature of 0° to 40° C., followed by reacting the resultant hydrochloride with 1.0 to 1.5 equivalents of sodium nitrite at -10° to 5° C. to form the diazonium salt. The diazonium salt is reduced with 3.0 to 10 equivalents (in regard to the aminosulfide (IV)) of stannous chloride at 0° to -40° C. to obtain the hydrazine hydrochloride, which is neutralized with an equeous alkaline solution (e.g. sodium hydroxide, potassium hydroxide, potassium carbonate) to obtain the hydrazine sulfide (V). The thus obtained hydrazine sulfide (V) is reacted with 1.0 to 1.2 equivalents of 2-alkoxycarbonylcyclohexanone in a solvent (e.g. acetic acid, toluene, xylene) at a temperature of 50° to 200° C. (preferably 80° to 150° C.) optionally while dehydrating by azeotropic distillation or in the presence of molecular sieve to give the hexahydroindazol-3-one (II).

Workup

  1. distillationwhile dehydrating by azeotropic distillation or in the presence of molecular sieve

Sources & evidence

ORD record
ord-92168e33961348d4aafe0b04763ad70b
Source dataset
uspto-grants-1990_06
Patent number
US04933480

Reaction notes

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