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

HRID 1958799Notes

Reaction equation

HRID 1958799 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 hydrazide

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 org. phase is collected, dried over MgSO4, filtered and evaporated to give the title compound as a yellow wax (24 g, 40% purity). 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. customphase is collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e5cb6489b35d41d2a6f0848f294c15e4
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

Loading…