Hydrochloric Acid → HCID 178487479, compound

HRID 453269Notes

Reaction equation

HRID 453269 reaction equation
C[C:2]1([N:9]=[N:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[CH:16][CH:17]=3)[CH:12]=2)[C:6](=O)[CH:5]=[C:4](C)[O:3]1.Cl>C(O)(=O)C>[OH:3][C:2]1[CH:6]=[C:5]([CH3:4])[N:10]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[CH:16][CH:17]=3)[CH:12]=2)[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86653537HCID 86653537, compound

Product 1

HCID 178487479HCID 178487479, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

2,5-dimethyl-2-(7-methoxynaphthalen-2-yldiazenyl)furan-3-one (3.4 g, 11.48 mmol) dissolved in acetic acid (20 ml) was added dropwise over hydrochloric acid 6N (3.5 ml) and was heated to a temperature of 60° C. The mixture was kept stirring at 60° C. during 2 hours. The solution was cooled, poured over a mixture of water/ice (400 ml) and the solid precipitate was filtered and washed with water. It was dried and a solid crude remained, which was purified by means of crystallization in toluene, thereby resulting in 1.23 g (42%) of 3-hydroxy-5-methyl-1-(7-methoxynaphthalen-2-yl)-1H-pyrazol in the form of a white-greyish coloured solid.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe solid precipitate was filtered
  3. washwashed with water
  4. customIt was dried
  5. customwhich was purified by means of crystallization in toluene
  6. customresulting in 1.23 g (42%) of 3-hydroxy-5-methyl-1-(7-methoxynaphthalen-2-yl)-1H-pyrazol in the form of a white-greyish coloured solid

Sources & evidence

ORD record
ord-4b0e9d03a61a4ae293b2754f570607ad
Source dataset
uspto-grants-2013_07
Patent number
US08492425B2

Reaction notes

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