Acetic Anhydride → 1,3-dihydro-3-acetoxy-3-(2-pyridinylmethyl)-1-(4-morpholinyl)-2H-indol-2-one

HRID 22239Notes

Reaction equation

HRID 22239 reaction equation
[OH:1][C:2]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:3]1=[O:17].[C:25](OC(=O)C)(=[O:27])[CH3:26]>CN(C)C1C=CN=CC=1.ClCCl>[C:25]([O:1][C:2]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:3]1=[O:17])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 233539751,3-dihydro-3-hydroxy-1-(4-morpholinyl)-3-(2-pyridinyl methyl)-2H-indol-2-one

Product 1

HCID 233539811,3-dihydro-3-acetoxy-3-(2-pyridinylmethyl)-1-(4-morpholinyl)-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of alcohol from Example 26 (63 mg, 0.194 mmole) 4-dimethylaminopyridine (78 mg, 0.639 mmole) , acetic anhydride (0.06 ml, 0.639 mmole) in dichloromethane (10 ml) was stirred at 0° C. for 8 hours. The volatiles were removed and the crude mixture applied directly to a silica gel column and eluted with 5% methanol in chloroform (Rf =0.34). The product slowly crystallized from hexane-ethyl acetate at 0° C. to give 41 mg of colorless cubes, m.p. 107°-110° C. after filtration. IR (KBr): 1702 cm-1. High Res. Mass Spec. Calcd. for C20H21N3O4 : 368.1610 (M+H) . Found: 368.1611.

Workup

  1. customThe volatiles were removed
  2. washeluted with 5% methanol in chloroform (Rf =0.34)
  3. customThe product slowly crystallized from hexane-ethyl acetate at 0° C.
  4. customto give 41 mg of colorless cubes, m.p. 107°-110° C.
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-bb2e6bf548e4488395eb657320d12624
Source dataset
uspto-grants-1995_06
Patent number
US05428035

Reaction notes

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