Ethanol → HCID 178433876, compound

HRID 1445320Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([OH:34])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[NH:33][N:32]=[N:31][N:30]=5)[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:35])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(O)C.[OH-].[OH:40][CH2:41][CH2:42][N+:43]([CH3:46])([CH3:45])[CH3:44].O>C(OCC)(=O)C.CO>[OH:40][CH2:41][CH2:42][N+:43]([CH3:46])([CH3:45])[CH3:44].[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[N:15][NH:16][C:17]3[C:18]([OH:34])=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]5[NH:30][N:31]=[N:32][N:33]=5)[CH:24]=4)[CH:20]=[CH:21][CH:22]=3)[C:11]([CH3:35])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 35 °C

Procedure

2-(3,4-Dimethylphenyl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one, 1.1 g of crude orange solid, in 7 mL of ethyl acetate and 12 mL of ethanol (190 proof) was stirred at approximately 40° C. To this suspension 2.5 ml of choline hydroxide (1N) solution in methanol was added resulting in a dark orange brown solution. Water (1 ml) was added to the dark solution and the mixture stirred at approx. 35° C. for approx. 3 hours. During this time, precipitation was seen in the solution. The suspension was stirred for another 72 hours at approx. 20° C., and then the solid was isolated by filtration and dried at approx. 40° C. over 12 hours to yield 1.2 gram (87% yield) of the title compound as a crystalline solid with a light orange color.

Workup

customresulting in a dark orange brown solution
customDuring this time, precipitation
stirringThe suspension was stirred for another 72 hours at approx. 20° C.
customthe solid was isolated by filtration
customdried at approx. 40° C. over 12 hours

Sources & evidence

ORD record: ord-952f0cb6e0454762b3aa534f4a1dd487
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666857B2

Reaction notes

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