Formic Acid → HCID 70216867, compound

HRID 2269779Notes

Reaction equation

HRID 2269779 reaction equation
C(N(CC)CC)C.C(O)=O.[CH3:11][N:12]([CH3:30])[C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:15]([N+:27]([O-])=O)[CH:14]=1>C(#N)C.[Pd]>[NH2:27][C:15]1[CH:14]=[C:13]([N:12]([CH3:30])[CH3:11])[CH:18]=[CH:17][C:16]=1[CH:19]=[C:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 70216993HCID 70216993, compound

Product 1

HCID 70216867HCID 70216867, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

In a dark room, 20.5 q (0.07 mol) of (E) ethyl 3-(4-dimethylamino-2-nitrophenyl)-2-methyl-2-propenate, 33.4 g (0.33 mol) of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.), and 2.1 g of 10% Pd/C were dissolved in 200 ml of acetonitrile, and 13.8 g (0.30 mol) of formic acid (manufactured by Wako Pure Chemical Industries, Ltd.) were added dropwise thereto at room temperature. Along with the dropping, the reaction temperature rose up to 45° C. After the completion of dropping, the reaction liquid was heated to 60° C. and was stirred for 1 hour. After the completion of the reaction was verified by TLC, the reaction liquid was cooled to room temperature, insoluble matters were filtered out, the filtrate was concentrated under a reduced pressure, and thus obtained product was dissolved in 400 ml of ethyl acetate. The resulting solution was successively washed with water, a saturated aqueous sodium hydrogencarbon ate solution, and a saturated aqueous sodium chloride solution; and was further dried with sodium sulfate anhydride. Thus dried product was concentrated under a reduced pressure, whereby 17.4 g of a crude product were obtained. This product was further recrystallized from normal hexane/ethyl acetate, whereby 4.67 g of the aimed compound were obtained (yield: 27%).

Workup

  1. customat room temperature
  2. customrose up to 45° C
  3. customthe reaction liquid
  4. customthe reaction liquid
  5. temperaturewas cooled to room temperature
  6. filtrationinsoluble matters were filtered out
  7. concentrationthe filtrate was concentrated under a reduced pressure, and thus obtained product
  8. dissolutionwas dissolved in 400 ml of ethyl acetate
  9. washThe resulting solution was successively washed with water
  10. dry with materialand was further dried with sodium sulfate anhydride
  11. concentrationThus dried product was concentrated under a reduced pressure
  12. customwhereby 17.4 g of a crude product were obtained
  13. customThis product was further recrystallized from normal hexane/ethyl acetate

Sources & evidence

ORD record
ord-8dfe5cc2f34c4b52b4ac55d43aa0aa36
Source dataset
uspto-grants-2001_12
Patent number
US06329546B1

Reaction notes

Loading…