Ammonia → HCID 66695349, compound

HRID 2367989Notes

Reaction equation

HRID 2367989 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[B:10]([OH:17])[O:11][CH:12]([CH2:13][N+:14]([O-])=O)[C:8]=2[C:7]([CH:18]=[CH2:19])=[CH:6][CH:5]=1)[CH3:2].N>CCO.[Ni]>[NH2:14][CH2:13][CH:12]1[O:11][B:10]([OH:17])[C:9]2[C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=[C:7]([CH:18]=[CH2:19])[C:8]1=2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 66692850HCID 66692850, compound

Product 1

HCID 66695349HCID 66695349, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 7-ethoxy-3-(nitromethyl)-4-vinylbenzo[c][1,2]oxaborol-1(3H)-ol (205 mg, 0.78 mmol), Raney-Ni (50 mg) and 2 M NH3 in EtOH (5 mL) in EtOH (10 mL) was shaken under an atmosphere of H2 for 2 h at room temperature. The mixture was filtered through a bed of Celite and the filtrate was concentrated in vacuo. The crude amine was dissolved in EtOAc (2 mL) and HCl in Et2O (20 mL) was added immediately. After 1 h, the suspension was filtered and the resulting solid was used directly for the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe crude amine was dissolved in EtOAc (2 mL)
  4. additionHCl in Et2O (20 mL) was added immediately
  5. waitAfter 1 h
  6. filtrationthe suspension was filtered
  7. customthe resulting solid was used directly for the next step without further purification

Sources & evidence

ORD record
ord-7163dacc20ea4d83a12b24e8b456592a
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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