Hydrazine hydrate (1:1) → HCID 13491283, compound

HRID 2417839Notes

Reaction equation

HRID 2417839 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][CH:9]([N:19]2C(=O)C3=CC=CC=C3C2=O)[C:8]1=[O:30])=[O:5])[CH3:2].O.NN>C(O)C>[NH2:19][CH:9]1[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:8]1=[O:30]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13338741HCID 13338741, compound

Product 1

HCID 13491283HCID 13491283, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-ethoxycarbonylmethyl-3-phthalimido-3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one (1.4 g) and hydrazine hydrate (0.19 g) in ethanol (400 ml) is refluxed for 4 hours. The solvent is removed under reduced pressure and the residue distributed between ethyl acetate (200 ml) and 2N hydrochloric acid (125 ml). The organic phase is washed with 2N hydrochloric acid (100 ml). The combined hydrochloric acid solutions are made strongly basic with 2N sodium hydroxide, extracted with ethyl acetate (2×200 ml), and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue recrystallized from ethanol/ether to give 3-amino-1-ethoxycarbonylmethyl-3,4,5,6-tetrahydro-1-benzazocin-2(1H)one as an oil, used without further purification in the next synthetic step.

Workup

  1. customThe solvent is removed under reduced pressure
  2. washThe organic phase is washed with 2N hydrochloric acid (100 ml)
  3. extractionextracted with ethyl acetate (2×200 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-f4de80c7cd944c2d91853ba87f4583ab
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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