Diazomethane → 4-Isopropoxybenzohydrazide

HRID 1386940

Reaction equation

HRID 1386940 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[N+:14](=C)=[N-:15].O.NN>C1COCC1>[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:14][NH2:15])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9550DiazomethaneHCID 24654Hydrazine hydrate (1:1)HCID 729724-Isopropoxybenzoic acid

Product 1

HCID 19904284-IsopropoxybenzohydrazideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-isopropoxy-benzoic acid (2.5 g, 13.8 mmol) in THF (5 ml) was treated with fresh ethereal diazomethane (ca. 20 mg/ml) (0.79 ml, 18.9 mmol, 1.4 eq.) at r.t. and stirred for 15 min. The crude product was then evaporated to dryness, dissolved in ethanol (10 ml) and heated under reflux with hydrazine monohydrate (3.5 ml, 71 mmol, 5 eq.) for 48 hrs. The volatiles were then completely evaporated and the product was dried overnight under high vacuum at 40° C. to afford the title compound (2.64 g, 99% yield) as a light brown solid. MS: m/e=194 (M+).

Workup

  1. customThe crude product was then evaporated to dryness
  2. dissolutiondissolved in ethanol (10 ml)
  3. temperatureheated
  4. customThe volatiles were then completely evaporated
  5. customthe product was dried overnight under high vacuum at 40° C.

Sources & evidence

ORD record
ord-8be0f680a8a040de99a1911215aa5f0e
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Linked notes

Loading…