1,1-Dimethylhydrazine → 1,3-Benzenedicarboxylic acid, monomethyl ester, 2,2-dimethylhydrazide

HRID 1784942Notes

Reaction equation

HRID 1784942 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])=[O:4].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:35][N:36]([CH3:38])[NH2:37].CCN(C(C)C)C(C)C>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:35][N:36]([CH3:38])[NH:37][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:9]

Participants

8

Reactant 5

HCID 59761,1-DimethylhydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 689609911,3-Benzenedicarboxylic acid, monomethyl ester, 2,2-dimethylhydrazideYield 60%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To the acid 3-(methoxycarbonyl)benzoic acid (253 mg, 1.40 mmol) in CH2Cl2 at rt, EDCI (312 mg, 1.64 mmol) and HOBT (189 mg, 1.40 mmol) were added and stirred at rt for 20 min. To that mixture, N,N-dimethyl hydrazine was added followed by DIPEA (404 mg, 14.0 mmol). Reaction mixture was stirred at rt for 16 h. Then reaction mixture was diluted with chloroform, washed with water, brine and dried. Crude residue was purified by column chromatography to yield 60% of methyl 3-(2,2-dimethylhydrazinecarbonyl)benzoate.

Workup

  1. customReaction mixture
  2. stirringwas stirred at rt for 16 h
  3. customThen reaction mixture
  4. washwashed with water, brine
  5. customdried
  6. customCrude residue was purified by column chromatography

Sources & evidence

ORD record
ord-2224827feb614d4dbaef6637acd0038d
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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