Acetic Anhydride → HCID 14249941, compound

HRID 867747Notes

Reaction equation

HRID 867747 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([OH:11])[CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]=12.C([O-])(O)=O.[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>S(=O)(=O)(O)O>[C:17]([O:11][C:4]1[CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]2=[C:2]([CH3:1])[N:3]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178433437HCID 178433437, compound

Product 1

HCID 14249941HCID 14249941, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 7-methylthieno[2,3-c]pyridin-5-ol (5.0 g, 30.3 mmol) and concentrated sulfuric acid (3 drops) in acetic anhydride (50 ml) was stirred at room temperature for 16 hours. The mixture was poured into ice water (300 ml), neutralized with NaHCO3, and was extracted with CH2Cl2. The organic layer was washed with a saturated solution of NaHCO3, dried over MgSO4, treated with activated charcoal and evaporated in vacuo to give the product (3.9 g, 62% yield) as an amber oil; IR (neat) 3090, 1770 and 1585 cm-1 ; mass spectrum m/z 207 (M+); 1H NMR (CDCl3) δ2.35 (s, 3H, COCH3), 2.75 (s, 3H, CH3), 7.28 (d superimposed on s, J=5 Hz, 2H, thiophene-H, Ar-H), 7.67 (d, J=5 Hz, 1H, thiophene-H).

Workup

  1. extractionwas extracted with CH2Cl2
  2. washThe organic layer was washed with a saturated solution of NaHCO3
  3. dry with materialdried over MgSO4
  4. additiontreated with activated charcoal
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1564166b269c4fa7ad43c4e117c08b17
Source dataset
uspto-grants-1988_10
Patent number
US04775757

Reaction notes

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