Hydrochloric Acid → 2-Butyryl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]-chromeno[6,5-g][1,8]naphthyridin-7-one

HRID 18040Notes

Reaction equation

HRID 18040 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:11][O:12][C:13]1[C:22]2[C:23](=[O:36])[C:24]3[CH:25]=[C:26]4[CH:35]=[CH:34][CH:33]=[CH:32][C:27]4=[N:28][C:29]=3[N:30]([CH3:31])[C:21]=2[C:20]2[CH:19]=[CH:18][C:17]([CH3:38])([CH3:37])[O:16][C:15]=2[CH:14]=1.Cl>ClCCl>[C:1]([C:18]1[C:17]([CH3:38])([CH3:37])[O:16][C:15]2[CH:14]=[C:13]([O:12][CH3:11])[C:22]3[C:23](=[O:36])[C:24]4[CH:25]=[C:26]5[CH:35]=[CH:34][CH:33]=[CH:32][C:27]5=[N:28][C:29]=4[N:30]([CH3:31])[C:21]=3[C:20]=2[CH:19]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 68586536HCID 68586536, compound

Product 1

HCID 685873612-Butyryl-6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]-chromeno[6,5-g][1,8]naphthyridin-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.81 mmol of butyryl chloride and 0.673 mmol of AlCl3 in 2 ml of anhydrous dichloromethane is added in small portions to 0.135 mmol of the product of Example 2 in 2 ml of dichloromethane at 0° C. The reaction mixture is stirred for 4 hours at ambient temperature and then poured into a 10% solution of HCl. Following conventional treatment of the organic phases, and evaporation thereof under reduced pressure, chromatography of the residue on silica gel (dichloromethane/methanol gradient) allows the expected product to be isolated.

Workup

  1. customtreatment of the organic phases, and evaporation
  2. customto be isolated

Sources & evidence

ORD record
ord-7f7b339957f84bd1aa5608085f6c63b5
Source dataset
uspto-grants-2010_06
Patent number
US07741325B2

Reaction notes

Loading…