Dimethylformamide → HCID 89657504, compound

HRID 521415Notes

Reaction equation

HRID 521415 reaction equation
O=[C:2]1[C:15]2[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[CH2:12][CH2:11][C:10]=2[NH:9][C:8]2[C:3]1=[C:4](C(O)=O)[CH:5]=[CH:6][CH:7]=2.[C:23]([O-:26])([O-])=[O:24].[K+].[K+].I[CH3:30].CN([CH:34]=[O:35])C>C(OCC)(=O)C>[CH3:34][O:35][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14]1[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=1[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][C:4]=2[C:23]([O:26][CH3:30])=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89657730HCID 89657730, compound

Product 1

HCID 89657504HCID 89657504, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 12-Oxo-5,6,7,12-tetrahydrobenzo[a]acridine-11-carboxylic acid (0.100 g, 0.34 mmol), K2CO3 (0.234 g, 1.7 mol), iodomethane (0.195 g, 1.37 mol), and DMF (1 mL) was stirred at room temperature for 16 hours, diluted with ethyl acetate (30 mL). The resulting mixture was washed with brine (6×5 ml), dried over Na2SO4, filtered, and concentrated. The remaining residue was chromatographed on silica gel using gradient eluant of 0-30% ethyl acetate in petroleum ether to give methyl 12-methoxy-5,6-dihydrobenzo[a]acridine-11-carboxylate as a light brown solid (20 mg, 56%). 1H NMR (CDC3-d1) δ8.24-8.25 (m, 1H), 8.04-8.06 (m, 1H), 7.76-7.79 (m, 1H), 7.53-7.54 (m, 1H), 7.36-7.40 (m, 3H), 4.03 (s, 3H), 3.66 (s, 3H), 3.16-3.18 (m, 2H), 3.03-3.06 (m, 2H). MS (ESI) m/e [M+1]+320.

Workup

  1. washThe resulting mixture was washed with brine (6×5 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe remaining residue was chromatographed on silica gel using gradient eluant of 0-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-5efb6a60b5d446beae997a673f791850
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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