Hydrochloric Acid → HCID 753926, compound

HRID 1679823Notes

Reaction equation

COC1C=C2C(=CC=1)[NH:12][C:11]1[C:10](=[O:16])[CH2:9][CH2:8][CH2:7][C:6]2=1.[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.Cl.[N+]([O-])([O-])=O.[Na+].[Na].C(=O)([O-])[O-].[Na+].[Na+].C([O-])(=O)C.[Na+]>CO.O>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][N:12]=[C:11]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]2=[O:16])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-methoxy-1,2,3,4-tetrahydrocarbazol-1-one 123 g. (1 mole) of p-methoxyaniline are dissolved in 600 ml. of water with the addition of 260 g. of concentrated hydrochloric acid. After cooling down to 0° C., 69 g. of sodium nitrate dissolved in 130 ml. of water are added dropwise to the solution. The diazotation being complete, 350 ml. of methanol and 148 g. (1 mole) of the sodium salt of the 1-hydroxymethylene-cyclohexanone are added and the temperature is maintained below +3° C. by adding ice. By the addition of 33.5 g. of anhydrous sodium carbonate and 250 g. of crystallized sodium acetate the solution is standardized to pH 5 to 6. After coupling is completed (10 to 12 hours or so), the solution is made up to a pH 9 to 9.5, stirred three hours at room temperature, filtered with suction and washed with water until free from alkali. Thus, cyclohexanedione-mono-p-methoxyphenylhydrazone is obtained which melts at 177° C. and has a yield of 202 g. (=87% of the theoretical).

Workup

temperaturethe temperature is maintained below +3° C.
additionby adding ice
additionBy the addition of 33.5 g
custom10 to 12 hours
filtrationfiltered with suction
washwashed with water until free from alkali

Sources & evidence

ORD record: ord-41f128d131054ebf8b35078b3587686a
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04271073

Reaction notes

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