Acetic Acid → HCID 58243054, compound

HRID 1894141Notes

Reaction equation

HRID 1894141 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([N+:17]([O-])=O)=[CH:4][N:3]=1.C(O)(=O)C>[Zn].CO>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[C:5]([NH2:17])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 58243047HCID 58243047, compound

Product 1

HCID 58243054HCID 58243054, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of Compound 1b (7.72 g; 27.4 mmol) in a mixture of glacial acetic acid (60 mL) and MeOH (120 mL) was added zinc dust (5.38 g; 82.2 mol) in portions at ambient temperature. The reaction mixture was stirred at room temperature for 20 h. The resultant mixture was filtered through a microglass filter and the filtrate was neutralized to pH 7 with 2 N KOH(aq). The mixture was partitioned between CH2Cl2 and H2O. The organic phase was washed sequentially with H2O and brine, and dried over Na2SO4. The mixture was filtered and the solvent was removed under reduced pressure to give the crude material. The crude material was purified by flash column chromatography (SiO2), eluting with a heptane-EtOAc gradient to afford Compound 1c (5.52 g; 80% yield) as an orange-red solid. 1H-NMR (400 MHz, CDCl3): δ 7.94 (s, 1H), 7.12-7.14 (m, 2H), 6.95-6.97 (m, 2H), 3.85 (s, 3H); MS: m/z 252.0 (M+H)+.

Workup

  1. filtrationThe resultant mixture was filtered through a microglass
  2. filtrationfilter
  3. customThe mixture was partitioned between CH2Cl2 and H2O
  4. washThe organic phase was washed sequentially with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe mixture was filtered
  7. customthe solvent was removed under reduced pressure
  8. customto give the crude material
  9. customThe crude material was purified by flash column chromatography (SiO2)
  10. washeluting with a heptane-EtOAc gradient

Sources & evidence

ORD record
ord-c88698d375b34cd6b0f36fa54656fad9
Source dataset
uspto-grants-2013_08
Patent number
US08513271B2

Reaction notes

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