Hydrazine hydrate (1:1) → HCID 178468570, compound

HRID 2225165Notes

Reaction equation

HRID 2225165 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5](=O)[CH2:6][C:7]([C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)=O)[CH3:2].O.[NH2:22][NH2:23]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[NH:22][N:23]=[C:7]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)[CH:6]=1)=[O:20])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 28397220ethyl 4-(adamantan-1-yl)-2,4-dioxobutanoate

Product 1

HCID 178468570HCID 178468570, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation C13, Step 2: 4-Adamantan-1-yl-2,4-dioxo-butyric acid ethyl ester 7.80 g, 28 mmol, 1 eq.), hydrazine hydrate (1.36 mL, 28 mmol, 1 eq.) and ethanol (20 mL) were refluxed until reaction was complete by LCMS. Stripped off the ethanol, and extracted (3×) with ethyl acetate (50 mL). The organic layers were combined, dried and stripped to give 7.00 g of 5-adamantan-1-yl-2H-pyrazole-3-carboxylic acid ethyl ester as a yellow solid. MS found: (M+H)+=275.

Workup

  1. customPreparation C13, Step 2
  2. extractionStripped off the ethanol, and extracted (3×) with ethyl acetate (50 mL)
  3. customdried

Sources & evidence

ORD record
ord-573f470c64a94fbb88ebaa0788571d21
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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