Hydrazine hydrate (1:1) → HCID 67230843, compound

HRID 1512003Notes

Reaction equation

HRID 1512003 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([N:12]2C(=O)C3C(=CC=CC=3)C2=O)[C:7]([Cl:11])=[C:8]([Cl:10])[CH:9]=1)=[O:4].O.NN>C(O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([NH2:12])[C:7]([Cl:11])=[C:8]([Cl:10])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67231054HCID 67231054, compound

Product 1

HCID 67230843HCID 67230843, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,5-dichloro-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester (5.44 g) and hydrazine monohydrate (1.57 mL) in ethanol was stirred at rt overnight, by which time TLC showed complete conversion; then the solids were filtered off, the filtrate was concentrated and worked up with EtOAc and water; EtOAc phase was washed with sat. NaCl solution and dried over anhydrous sodium sulfate, filtered, concentrated, the crude was column purified (EtOAc/Hexanes) to give desired product (2.21 g). ESI (m/z): 209 (M+H)+.

Workup

  1. filtrationthen the solids were filtered off
  2. concentrationthe filtrate was concentrated
  3. washEtOAc phase was washed with sat. NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified (EtOAc/Hexanes)

Sources & evidence

ORD record
ord-1e77a86942604c54a7df23c390b44090
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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