Acetic Anhydride → HCID 86597338, compound

HRID 858157Notes

Reaction equation

HRID 858157 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=O)=O)[CH:8]=2)[NH:3]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(=O)C.[Na+]>[Zn].C(O)(=O)C>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:16](=[O:18])[CH3:17])[CH:8]=2)[NH:3]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 534146522-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride

Product 1

HCID 86597338HCID 86597338, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To an ice bath cooled, stirred mixture of impure 2-Oxo-1,2-dihydro-quinoline-6-sulfonyl chloride (20 g, ˜82 mmol), acetic acid (240 cm3) and acetic anhydride (80 cm3) was added sodium acetate (24 g) in three equal sized batches. Then Zinc (20 g) was added in small batches (exothermic reaction). After one hour the ice bath was removed and the reaction was left stirring at room temperature for five days then concentrated in vacuo then triturated with water (˜200 cm3). The solid that was formed was filtered off and dried in vacua to yield Thioacetic acid S-(2-oxo-1,2-dihydro-quinolin-6-yl) ester as a dry grey solid (11.7 g, ˜65%); δH (300 MHz; D6 DMSO) 2.42 (3H, s, COCH3), 6.51–6.57 (1H, m, Ar—H), 7.32–7.37 (1H, m, Ar—H), 7.43–7.48 (1H, m, Ar—H), 7.72 (1H, s, Ar—H), 7.88–7.92 (1H, m, Ar—H) and 11.95 (1H, br s, N—H); LCMS retention time ˜3.03 min, m/z (FIAPOS) 220 [(M+H)+, 100%].

Workup

  1. temperatureTo an ice bath cooled
  2. customAfter one hour the ice bath was removed
  3. waitthe reaction was left
  4. stirringstirring at room temperature for five days
  5. concentrationthen concentrated in vacuo
  6. customthen triturated with water (˜200 cm3)
  7. customThe solid that was formed
  8. filtrationwas filtered off
  9. customdried in vacua

Sources & evidence

ORD record
ord-5a01330cd01a4bd7a7600687488ba38c
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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