Hydrazine hydrate (1:1) → HCID 65343348, compound

HRID 871075Notes

Reaction equation

HRID 871075 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:16]=1)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.O.NN>CO.O.[Ni]>[Br:1][C:2]1[CH:16]=[C:6]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[C:5]([NH2:17])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 24902991HCID 24902991, compound

Product 1

HCID 65343348HCID 65343348, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To suspension of Example 2A (700 mg, 2.153 mmol) in methanol (10 mL) was added hydrazine monohydrate (0.2 mL, 4.08 mmol) followed by 50% Raney® nickel in water (100 mg). The mixture was stirred at 50° C. for 2 hours, filtered through diatomaceous earth with dichloromethane and concentrated. Purification by flash chromatography (Isco®, Redi-Sep® column) eluting with 100% dichloromethane gave the title compound.

Workup

  1. filtrationfiltered through diatomaceous earth with dichloromethane
  2. concentrationconcentrated
  3. customPurification by flash chromatography (Isco®, Redi-Sep® column)
  4. washeluting with 100% dichloromethane

Sources & evidence

ORD record
ord-052541c1a98b4645aed729bb6d165e0d
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

Loading…