Hydrazine hydrate (1:1) → HCID 20231445, compound

HRID 2290553Notes

Reaction equation

HRID 2290553 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:9][C:8]=2[O:24][CH3:25])=[CH:4][CH:3]=1.O.NN>C(O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[O:24][CH3:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13768630HCID 13768630, compound

Product 1

HCID 20231445HCID 20231445, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2.5 g (0.007 mole) of 2-[4-(5-chlorothien-2-yl)-3-methoxyphenyl]-1H-isoindol-1,3(2H)-dione and 0.4 g (0.007 mole) of hydrazine hydrate in 30 ml of absolute ethanol was heated at reflux for one hour. The mixture was cooled and the solvent evaporated under reduced pressure to leave a residue. The residue was subjected to column chromatography on silica gel, eluting with methylene chloride to yield 1.4 g of 4-(5-chlorothien-2-yl)-3-methoxyaniline.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. temperatureThe mixture was cooled
  4. customthe solvent evaporated under reduced pressure
  5. customto leave a residue
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-f7d66abdb7754a1583a444f63a302e1b
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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