Acetic Anhydride → HCID 178454361, compound

HRID 37450Notes

Reaction equation

HRID 37450 reaction equation
[C:1]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17]1(=O)[O:22][C:20](=[O:21])[CH:19]=[CH:18]1.C(OC(=O)C)(=O)C.C(N(CC)CC)C>CC(C)=O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:1]([NH:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]2=[O:22])=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 103763392-BOC-hydrazino-5-amino pyridine

Product 1

HCID 178454361HCID 178454361, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-BOC-hydrazino-5-amino pyridine (1 equivalent) in acetone (50 ml/gm) was added maleic anhydride (1.1 equivalents). The reaction mixture was stirred at 25° for 2 hours. To the reaction mixture was added acetic anhydride (1.2 equivalents), cobalt acetate (0.007 equivalents) and triethylamine (0.3 equivalents). The reaction mixture was stirred at 60° for 2 hours. The color of the reaction began as bright yellow and ended as dark yellow. The reaction mixture was concentrated under reduced pressure to give a yellow brown oil. Flash vacuum chromatography (hexanes/ethyl acetate (8/2)) was used to isolate the product. The product was recrystallized in ether/hexane; yield 28.3%; m.p. 182°-184°. IR (KBr): 3400, 3300, 3100, 2990, 1700, 1610, 1500, 1410, 1360, 1320, 1270, 1210, 1150, 1050, 830, 750, 690 cm-1.

Workup

  1. stirringThe reaction mixture was stirred at 60° for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a yellow brown oil
  4. customto isolate the product
  5. customThe product was recrystallized in ether/hexane

Sources & evidence

ORD record
ord-a9e1d90b102749fab1342dfcf79bf561
Source dataset
uspto-grants-1995_05
Patent number
US05420285

Reaction notes

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