Hydrazine → 4-Benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide

HRID 1685732Notes

Reaction equation

HRID 1685732 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:19][CH3:20])(C)[CH2:11][C:12](=[CH:16][CH:17]=1)[C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21]CN(C(C)C)C(C)C.C1CN([P+](O[N:47]2[N:55]=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.NN>C(Cl)Cl.C1COCC1>[CH2:1]([O:8][C:9]1[C:17]([CH3:21])=[CH:16][C:12]([C:13]([NH:47][NH2:55])=[O:15])=[CH:11][C:10]=1[CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 66932377HCID 66932377, compound

Product 1

HCID 592020264-Benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazideYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyloxy-3-ethyl-3-methyl-benzoic acid (8.3 g, 30.7 mmol) in DCM (300 mL) is added DIPEA (10.7 mL) and the mixture is cooled to 0° C. before PyBOP (14.5 g, 33.8 mmol) is added. After 10 min, a solution of 1M hydrazine in THF (100 mL) is added dropwise and the mixture is slowly warmed to rt during 2 h. The reaction mixture is then washed with sat. aq. NaHCO3 followed by brine. The organic phase is collected, dried over MgSO4, filtered and evaporated to give the title compound (24 g, 40% purity) as a yellow wax; LC-MS: tR=0.82 min; [M+H]+=285.10.

Workup

  1. additionis added
  2. washThe reaction mixture is then washed with sat. aq. NaHCO3
  3. customThe organic phase is collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1f269ac3362742f2adfd49849e7223f8
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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