Hydrazine hydrate (1:1) → HCID 20269930, compound

HRID 485283Notes

Reaction equation

HRID 485283 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=2)C(=O)C2=CC=CC=C12.O.NN>CO>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20269948HCID 20269948, compound

Product 1

HCID 20269930HCID 20269930, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With 6.88 g (17.5 mmols) of t-butyl 3-[4-(3-phthalimidopropyl)phenyl]propionate were admixed 1.10 ml (22.8 mmols) of hydrazine hydrate and 50 ml of methanol. The mixture was refluxed for 1 hour, cooled to room temperature and then concentrated. The concentrate was dissolved in 200 ml of 1 mol dm-3NaOH, followed by extraction with ether. The extract was dried over K2CO3 and concentrated to give 4.14 g (yield 90%) of t-butyl 3-[4-(3-aminopropyl)phenyl]propionate in the form of an oil.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in 200 ml of 1 mol dm-3NaOH
  4. extractionfollowed by extraction with ether
  5. dry with materialThe extract was dried over K2CO3
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a869b38182c4386a1d475bfce3ce50e
Source dataset
uspto-grants-1985_08
Patent number
US04536391

Reaction notes

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