Hydrazine → 3-[(Ethyl-methyl-amino)-methyl]-5-methyl-benzoic acid hydrazide

HRID 1958811Notes

Reaction equation

HRID 1958811 reaction equation
[CH2:1]([N:3]([CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:9](O)=[O:10])[CH3:4])[CH3:2].C1CN([P+](O[N:33]2[N:41]=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.NN>C1COCC1.CC(=O)OCC>[CH2:1]([N:3]([CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:9]([NH:33][NH2:41])=[O:10])[CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 669323243-[(Ethyl-methyl-amino)-methyl]-5-methyl-benzoic acid

Product 1

HCID 669323583-[(Ethyl-methyl-amino)-methyl]-5-methyl-benzoic acid hydrazideYield 278.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[(ethyl-methyl-amino)-methyl]-5-methyl-benzoic acid (215 mg, 1.04 mmol) in THF (5 mL), PyBOP (541 mg, 1.04 mmol) followed by DIPEA (269 mg, 2.08 mmol) is added. The mixture is stirred until all solid material has dissolved and is then transferred into a 1M solution of hydrazine in THF (8.3 mL; 266 mg, 8.33 mmol). The resulting suspension is stirred at rt for 1 h before it is diluted with EA and washed with water. The org. extract is concentrated and dried to give the crude title compound as a white solid (640 mg). LC-MS: tR=0.35 min, [M+1]+=222.05.

Workup

  1. additionis added
  2. dissolutionhas dissolved
  3. stirringThe resulting suspension is stirred at rt for 1 h before it
  4. washwashed with water
  5. extractionextract
  6. concentrationis concentrated
  7. customdried

Sources & evidence

ORD record
ord-948ab302db3a474d846af67cabf06095
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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