Hydrazine hydrate (1:1) → Methyl 3-(4-aminobutoxy)benzoate

HRID 1594435Notes

Reaction equation

HRID 1594435 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])C(=O)C2=CC=CC=C12.O.NN>C(O)C.C(Cl)(Cl)Cl>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58678553Methyl 3-(4-phthalimidobutoxy)benzoate

Product 1

HCID 58678502Methyl 3-(4-aminobutoxy)benzoateYield 115.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-(4-phthalimidobutoxy)benzoate (6.60 g, 18.68 mmol) was dissolved in 50 mL of ethanol and reacted with hydrazine monohydrate (1.87 g, 37.36 mmol). Following stirring at 80° C. for 1 hour, the resulting mixture was diluted with chloroform, then washed with a saturated sodium bicarbonate solution, water, and brine, and dried with sodium sulfate. The resulting reaction solution was concentrated under reduced pressure to give a white crystal (4.81 g). The white crystal was directly used in subsequent reaction.

Workup

  1. washwashed with a saturated sodium bicarbonate solution, water, and brine
  2. dry with materialdried with sodium sulfate
  3. customThe resulting reaction solution
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb0fefb886df4bbb97d68c53fc4a3eb7
Source dataset
uspto-grants-2007_11
Patent number
US07301033B2

Reaction notes

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