Isoniazid → HCID 178465646, compound

HRID 418269Notes

Reaction equation

HRID 418269 reaction equation
[OH:1][C@H:2]([C:9]1[N:10]=[C:11]([C:14](=O)[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6].[C:17]([NH:25][NH2:26])(=[O:24])[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>C(O)C.O.Cl>[OH:1][C@H:2]([C:9]1[N:10]=[C:11](/[C:14](=[N:26]/[NH:25][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)/[CH3:15])[NH:12][CH:13]=1)[C@H:3]([OH:8])[C@H:4]([OH:7])[CH2:5][OH:6]

Participants

6

Reactant 2

HCID 3767IsoniazidHCID 178467425HCID 178467425, compound

Product 1

HCID 178465646HCID 178465646, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (168 mg, 0.73 mmol) was suspended in ethanol (4 ml) and water (1 ml). Isonicotinic hydrazide (110 mg, 0.80 mmol, 1.1 eq.) and hydrochloric acid (one drop, 12 N) were added, and the suspension was stirred at 55° C. for 24 hours. LCMS analysis indicated the formation of the product and the absence of starting material. The reaction mixture was cooled to room temperature, and partially concentrated in vacuo. The resulting white precipitate was collected and washed with ethanol to yield the product, as one apparent isomer, as a white solid: 136 mg (75%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationpartially concentrated in vacuo
  3. customThe resulting white precipitate was collected
  4. washwashed with ethanol
  5. customto yield the product

Sources & evidence

ORD record
ord-970fc718c48343c0be24b13502ea9bb1
Source dataset
uspto-grants-2012_01
Patent number
US08093267B2

Reaction notes

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