Pyridine → HCID 19906358, compound

HRID 2371788Notes

Reaction equation

HRID 2371788 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:19]1([CH2:24][C:25](Cl)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl>[CH:19]1([CH2:24][C:25]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][C:9]3=[O:12])=[CH:4][CH:3]=2)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-oneHCID 3485182Cyclopentylacetyl chloride

Product 1

HCID 19906358HCID 19906358, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 7-amino-1-tetralone (13.2 g) (prepared as described above and used without further purification) and pyridine (8.4 ml) in methylene chloride (130 ml) at 0° C. was added a solution of cyclopentylacetyl chloride (13.2 g) in methylene chloride (20 ml). The reaction was stirred for 30 min and at room temperature for 1.5 h. The mixture was evaporated and the residue was diluted with ethyl acetate, washed (saturated sodium bicarbonate, 1N HCl, brine), dried (MgSO4) and evaporated. The residue was flash chromatographed, eluting with ethyl acetate:methylene chloride (5:95, 7.5:92.5, and 1:9, successively), to give 7-cyclopentylacetamido-1-tetralone (16.6 g, 74%) as a colorless solid; mp 117.0°-118.0° C.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed (saturated sodium bicarbonate, 1N HCl, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customchromatographed
  7. washeluting with ethyl acetate:methylene chloride (5:95, 7.5:92.5, and 1:9

Sources & evidence

ORD record
ord-52ccc3c9d206421291397228dab35c2d
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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