Sodium Bicarbonate → 8-Aminospiro[3.5]non-7-EN-6-one

HRID 573756Notes

Reaction equation

HRID 573756 reaction equation
[OH:1][C:2]1[CH2:10][C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:5][C:4](=O)[CH:3]=1.C([O-])(=O)C.[NH4+:16].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[NH2:16][C:4]1[CH2:5][C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:10][C:2](=[O:1])[CH:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 211332648-Hydroxyspiro[3.5]non-7-en-6-one

Product 1

HCID 667614868-Aminospiro[3.5]non-7-EN-6-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

10 g 8-hydroxyspiro[3.5]non-7-en-6-one and 10.1 g ammonium acetate are dissolved in 100 ml toluene and 3.2 ml acetic acid. The mixture is refluxed for 2 hours using a Dean-Stark trap. After cooling to room temperature the mixture is cautiously added to 200 ml of a saturated solution of sodium bicarbonate and 100 g ice. Then the mixture is stirred for 15 minutes, the solid product is collected by filtration and dried at 50° C. in vacuo.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. filtrationthe solid product is collected by filtration
  3. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-b45f53fe787c4b2aa35b8b1646ab0e5f
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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