Formic Acid → HCID 11116940, compound

HRID 863205Notes

Reaction equation

HRID 863205 reaction equation
C(O)=O.Cl[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C>C(#N)C.[Pd]>[N+:16]([C:6]1[CH:7]=[C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])[CH:9]=[CH:10][CH:5]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 11064234HCID 11064234, compound

Product 1

HCID 11116940HCID 11116940, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

16.5 ml of formic acid are added over 5 minutes to a round-bottomed flask, under inert atmosphere, containing 67.7 g of (RS)-2-(4-chloro-3-nitrophenyl) propionic acid, 87 ml of triethylamine and 6.1 g of 5% palladium-on-charcoal in 680 ml of acetonitrile. The reaction medium is heated at reflux for 18 hours and, after cooling to a temperature in the region of 20° C., is then filtered through Celite. The filtrate is evaporated to dryness under reduced pressure and taken up in 500 ml of water and 400 ml of ethyl acetate. The organic phase is separated out after settling has taken place and the aqueous phase is extracted with twice 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulphate and concentrated to dryness under reduced pressure at 40° C. 53 g of 2-(3-nitrophenyl)propionic acid are thus obtained in the form of a brown oil [IR spectrum (CH2 Cl2, cm-1) δOH acid: 3250-2450; γCH Aliph.: 2985-2940; γC=0: 1715; γaNO2 : 1535; γsNO2 : 1355; γPh m-subst.: 690; NMR spectrum (DMSO-d6, 200 MHz): 1.45 (d, J=7 Hz, 3H); 3.9 (q, J=7 Hz, 1H); 7.6 (t, J=7 Hz, 1H); 7.8 (d, J=7 Hz, 1H); 8.1 (d, J=7 Hz, 1H); 8.15 (s, 1H); 12.5 (broad s, acidic OH)].

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for 18 hours
  3. filtrationis then filtered through Celite
  4. customThe filtrate is evaporated to dryness under reduced pressure
  5. customThe organic phase is separated out after settling
  6. extractionthe aqueous phase is extracted with twice 200 ml of ethyl acetate
  7. dry with materialThe combined organic phases are dried over magnesium sulphate
  8. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-bbc2c855b22b4f04b7ff0e02b0055808
Source dataset
uspto-grants-1998_02
Patent number
US05719317

Reaction notes

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