Tetrahydrofuran → Ethyl 4-(3-(naphthalen-2-yl)propanamido)benzoate

HRID 2422946Notes

Reaction equation

HRID 2422946 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[O:14].C1COCC1>CO.Cl[Ni]Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1)=[O:14]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67243223Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate

Product 1

HCID 24782383Ethyl 4-(3-(naphthalen-2-yl)propanamido)benzoateYield 79%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

Ref. J. of Org. Chem., 2000, 65, 8001. To a stirred solution of amide 42 (0.086 g, 0.249 mmol) and NiCl2 6H2O (0.118 g, 0.498 mmol, 2 eq) in methanol (8 ml) and THF (4 ml) NaBH4 (0.028 g, 0.749 mmol, 4 eq) was added portionwise over 20 min at 0° C. After stirring for 1 h at room temperature, the solvent was distilled off under reduced pressure. Water (10 ml) and ethyl acetate (10 ml) was added. The resulting mixture was filtered through a celite bed which was washed with ethyl acetate (20 ml). After collecting the filtrate, the organic phase was separated, dried over Na2SO4 and the solvent was distilled off under reduced pressure to give the pure product 69 as a white solid (0.066 g, 0.190 mmol, 79%), mp 119-121° C. 1H NMR (400 MHz, CDCl3) δ 1.38 (3H, t, J 7.2 Hz, CH2CH3) 2.75 (2H, t, J 7.2 Hz, CH2CO), 3.23 (2H, t, J 7.2 Hz, CH2—Ar), 4.35 (2H, q, J 7.2 Hz, CH2CH3), 7.12 (1H, bs, N—H), 7.37 (1H, dd, J 1.6, 8.4 Hz, CH, Ar), 7.42-7.50 (4H, m, 4×CH, Ar), 7.69 (1H, bs, CH, Ar), 7.76-7.82 (3H, m, 3×CH, Ar), 7.97 (2H, d, J 9.2 Hz, 2×CH, Ar). MS (API-ES): m/z 348 [M+H]+ (100%), HRMS (API-ES) m/z found 348.1602 [M+H]+.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater (10 ml) and ethyl acetate (10 ml) was added
  3. filtrationThe resulting mixture was filtered through a celite bed which
  4. washwas washed with ethyl acetate (20 ml)
  5. customAfter collecting the filtrate
  6. customthe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9b53b3bc347f41958ca4f2bbeb78fdd6
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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