Hydrazine hydrate (1:1) → HCID 11620054, compound

HRID 1261546Notes

Reaction equation

HRID 1261546 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:38][CH:37]=3)[CH:19]=[CH:20][C:21]=2[CH2:22][CH2:23][CH2:24][N:25]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:38][CH:37]=3)[CH:19]=[CH:20][C:21]=2[CH2:22][CH2:23][CH2:24][NH2:25])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66672038HCID 66672038, compound

Product 1

HCID 11620054HCID 11620054, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a 50 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer, 900 mg (1.46 mmol) of ethyl 3″-tert-butyl-4″-diethylamino-4′-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]-[1,1′;3′,1″]terphenyl-4-carboxylate and 292 mg (5.8 mmol) of hydrazine hydrate are placed in 20 mL of ethanol. The reaction medium is heated to the reflux point of the ethanol for 20 hours and then filtered; the filtrate obtained is evaporated and then purified directly on a column of silica (eluent: 94/6 dichloromethane/methanol) to give, after evaporation of the purest fractions, 545 mg of ethyl 3″-tert-butyl-4′-(3-aminopropyl)-4″-diethylamino[1,1′;3′,1″]terphenyl-4-carboxylate (yield=77%) in the form of a colorless oil.

Workup

  1. customIn a 50 mL three-necked flask under a nitrogen atmosphere, equipped with a magnetic stirrer
  2. filtrationfiltered
  3. customthe filtrate obtained
  4. customis evaporated
  5. custompurified directly on a column of silica (eluent: 94/6 dichloromethane/methanol)
  6. customto give

Sources & evidence

ORD record
ord-f07f0094ce5e4b7db34265cc75eef095
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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