Acetic Acid → CI-923

HRID 851215Notes

Reaction equation

HRID 851215 reaction equation
O=[C:2]([CH3:19])[CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[O:12][C:13](=[O:14])[C:6]=2[CH2:5]1.[CH2:20]([NH2:22])[CH3:21].S([O-])([O-])(=O)=O.[Ca+2].C(O)(=O)C>O1CCCC1>[CH2:20]([NH:22][CH:2]([CH3:19])[CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[O:12][C:13](=[O:14])[C:6]=2[CH2:5]1)[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 24497Calcium SulfateHCID 131369403-(2-oxopropyl)-1,2,3,4-tetrahydro-5H-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 135209CI-923Yield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1,2,3,4-tetrahydro-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one (18.2 g, 0.071 moles), ethylamine (10 ml, 0.153 moles), anhydrous calcium sulfate (15 g), and glacial acetic acid (1 ml) in tetrahydrofuran (450 ml) is shaken at 40° C. in a pressure vessel. After 18 hours the mixture is cooled and filtered. The filtrate is hydrogenated at 25° C. and 50 psi in the presence of 10% platinum or carbon until hydrogen uptake ceases. The catalyst is removed by filtration, and the filtrate is evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate gave the product (10.5 g), mp 104°-105° C.

Workup

  1. temperatureAfter 18 hours the mixture is cooled
  2. filtrationfiltered
  3. customis hydrogenated at 25° C.
  4. customThe catalyst is removed by filtration
  5. customthe filtrate is evaporated under reduced pressure
  6. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-406418d0fbf74a10a2a32dab733715ab
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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