Methanol → HCID 3072388, compound

HRID 495606Notes

Reaction equation

HRID 495606 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C@@H:9]2[CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:6][CH:7]=1.CO>C(O)C.O.NN.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C@@H:9]2[CH2:13][NH2:14])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 887MethanolHCID 69796332HCID 69796332, compound

Product 1

HCID 3072388HCID 3072388, compoundYield 104.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A solution of D6 (5.80 g, 0.018 mol) in ethanol (60 ml) and hydrazine hydrate (2 .eq., 2 ml) was heated at reflux for 1 h and cooled. The resulting precipitate was filtered and filtrate concentrated under reduced pressure to leave an oil. Chromatography on silica gel eluting with methanol in DCM (gradient elution, maximum 10%) afforded the product as an oil (3.58 g, 94%).

Workup

  1. temperatureat reflux for 1 h
  2. temperaturecooled
  3. filtrationThe resulting precipitate was filtered
  4. concentrationfiltrate concentrated under reduced pressure
  5. customto leave an oil

Sources & evidence

ORD record
ord-752a6dbb4a54467eb71d7614a19d7490
Source dataset
uspto-grants-2005_09
Patent number
US06939891B2

Reaction notes

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