HCID 966370, compound → HCID 66860046, compound

HRID 252308Notes

Reaction equation

HRID 252308 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([CH3:14])[C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>C1COCC1.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]([CH3:14])[C:11]([NH2:13])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 966370HCID 966370, compoundHCID 2723923Ammonium formate

Product 1

HCID 66860046HCID 66860046, compoundYield 96.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

(2R)-2-(4-Nitrophenyl)propanamide (4.9 g, 25.2 mmol) was dissolved in a mixture of THF (30 mL) and CH3OH (30 mL) and the resulting solution cooled at T=0-5° C. Ammonium formate (8 g, 126.mmol) was added and, then, also 10% Pd/C (1.6 g) was added portionwise and carefully. The resulting mixture was left stirring at room temperature overnight, until complete disappearance of the starting material (by TLC). After under vacuum filtration over a celite cake, and solvents evaporation at reduced pressure, the pure (2R)-2-(4-aminophenyl)propanamide was isolated as white powder (4 g, 24.24 mmol). Yield 96.2%. m.p. 110-112° C.; [α]D25 (c=0.6, CH3OH): −1.9°; 1H-NMR (CDCl3) δ 7.10 (d, 2H, J=7 Hz), 6.65 (d, 2H, J=7 Hz), 5.35 ((bs, 2H, CONH2), 3.52 (m, 1H), 1.50 (d, 3H, J=7 Hz).

Workup

  1. waitThe resulting mixture was left
  2. filtrationAfter under vacuum filtration
  3. customover a celite cake, and solvents evaporation at reduced pressure

Sources & evidence

ORD record
ord-a0ff7581a37f44cab13f6647a666693e
Source dataset
uspto-grants-2011_01
Patent number
US07868046B2

Reaction notes

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