Nicotinic acid, hydrazide → HCID 178465642, compound

HRID 1169861Notes

Reaction equation

HRID 1169861 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][CH:21]=[N:20][CH:19]=1>CO.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][CH:21]=[N: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 11112Nicotinic acid, hydrazideHCID 178467425HCID 178467425, compound

Product 1

HCID 178465642HCID 178465642, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-[4-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-1H-imidazol-2-yl]-ethanone (215 mg, 0.93 mmol) was suspended in methanol (3 ml) and water (1 ml). Nicotinic acid hydrazide (137 mg, 1.0 mmol, 1.1 eq.) and hydrochloric acid (one drop, 12 N) were added, and the suspension was stirred at 50° C. for 48 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 water to yield the product, one apparent isomer, as a white solid: 311 mg (95%).

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 water
  5. customto yield the product, one apparent isomer

Sources & evidence

ORD record
ord-53a0044d0d0442e9b544a5ec44d11848
Source dataset
uspto-grants-2010_11
Patent number
US07825150B2

Reaction notes

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