Methane → HCID 10727244, compound

HRID 566470Notes

Reaction equation

HRID 566470 reaction equation
[C:1]([NH:4][C:5]1[C:6](=[O:17])[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[NH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=O)[CH3:2].C>C(O)(=O)C.[Zn]>[CH3:2][C:1]1[NH:15][C:14]2[C:13](=[O:16])[C:12]3[C:7]([C:6](=[O:17])[C:5]=2[N:4]=1)=[CH:8][CH:9]=[CH:10][CH:11]=3

Participants

5

Reactant 2

HCID 297MethaneHCID 337349ST4097063

Product 1

HCID 10727244HCID 10727244, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Method 2 (Acid-Promoted Cyclization): A solution of 3a (2.0 g, 0.0009 mol) and Zn (1.0 g) in glacial acetic acid (50 ml) was refluxed for 24 h. A small amount of activated charcoal was added, and the solution was then filtered. The filtrate was poured into a 4-fold excess of H2O. The pH was adjusted to 8 by addition of a solution of NaHCO3, and the resulting solution was then filtered. The recovered precipitate was recrystallized from EtOH to give a dark brown powder (4a).

Workup

  1. filtrationthe solution was then filtered
  2. additionThe filtrate was poured into a 4-fold excess of H2O
  3. additionThe pH was adjusted to 8 by addition of a solution of NaHCO3
  4. filtrationthe resulting solution was then filtered
  5. customThe recovered precipitate was recrystallized from EtOH

Sources & evidence

ORD record
ord-e72ad82953dd457b877a0ba4e6821422
Source dataset
uspto-grants-2001_01
Patent number
US06174918B1

Reaction notes

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