Hydrazine → HCID 21104165, compound

HRID 1354817Notes

Reaction equation

HRID 1354817 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:24][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=1[OH:23])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NN>CO.C1COCC1.[Ni]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:24]=[CH:25][C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:27][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:15]([OH:23])[CH:16]=1

Participants

6

Reactant 2

HCID 9321HydrazineHCID 21103673HCID 21103673, compound

Product 1

HCID 21104165HCID 21104165, compoundYield 59.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 39 (470 mg, 1 mmol) was dissolved in MeOH (15 mL) and THF (15 mL). Raney Nickel (50% slurry in water) (2 mL) was added to the reaction mixture followed by anhydrous hydrazine (1 mL). The reaction mixture was stirred at room temperature for 30 minutes until the bubbling was stopped. The solid was filtered off through Celite under reduced pressure and washed with MeOH. The solvent was removed under reduced pressure. Liquid-liquid extraction was performed using CHCl3 (15 mL) and H2O (8 mL×2). The organic layer was dried over MgSO4, filtered and concentrated to give the compound 40 (263.8 mg, 59.9% crude yield) LC-MS (ESI): m/e=441.1 [M+1]+

Workup

  1. filtrationThe solid was filtered off through Celite under reduced pressure
  2. washwashed with MeOH
  3. customThe solvent was removed under reduced pressure
  4. extractionLiquid-liquid extraction
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9d490996b5764c038fde2d1df3de17c0
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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