Hydrochloric Acid → 1-(3-methyl-1H-indazol-1-yl)Ethanone

HRID 2118479Notes

Reaction equation

HRID 2118479 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.N1C=CC=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>C(#N)C>[C:17]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[N:3]1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178434273HCID 178434273, compound

Product 1

HCID 126391861-(3-methyl-1H-indazol-1-yl)EthanoneYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

290 g (2.20 mol) of 3-methylindazole and an acetonitrile solution (400 ml) of pyridine (4.34 mol) were stirred as the mixture was cooled on a water bath, and 310 ml (3.30 mol) of acetic anhydride was added dropwise thereto. Upon addition, the reaction temperature rose from 15° C. to 43° C. After the conclusion of the dropwise addition, the reaction solution was warmed to from 55° to 60° C., and stirred at this temperature for one hour. After cooling to 20° C., the reaction solution was poured into 1.5 kg of ice-cold water containing 500 ml of aqueous hydrochloric acid. The crystals deposited were filtered off, and washed with water. Thus, 328 g (1.89 mol) of 1-acetyl-3-methylindazole was obtained.

Workup

  1. temperaturewas cooled on a water bath
  2. additionUpon addition
  3. customrose from 15° C. to 43° C
  4. additionAfter the conclusion of the dropwise addition
  5. temperaturethe reaction solution was warmed to from 55° to 60° C.
  6. filtrationThe crystals deposited were filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-dd59210a924b4654b8cc8f7ad61edb2a
Source dataset
uspto-grants-1987_07
Patent number
US04678739

Reaction notes

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