Methyl iodide → HCID 131710522, compound

HRID 1729990Notes

Reaction equation

HRID 1729990 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]([O:28][CH3:29])=[CH:7][C:8]2[C:17]3[CH2:16][CH2:15][N:14]([C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]=3[C:11](=O)[NH:10][C:9]=2[CH:27]=1.[CH3:30]I>CN(C)C=O>[CH3:3][O:4][C:5]1[C:6]([O:28][CH3:29])=[CH:7][C:8]2[C:17]3[CH2:16][CH2:15][N:14]([C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][C:12]=3[CH2:11][N:10]([CH3:30])[C:9]=2[CH:27]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21793849HCID 21793849, compound

Product 1

HCID 131710522HCID 131710522, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of 0.017 m of NaH (washed with petroleum ether) in 50 ml of dimethyl formamide was treated in portions with 5 g (0.0137 m) of 1,2,3,4-tetrahydro-8,9-dimethoxy-3-benzoyl-benzo[c][2,7]naphthyridin-5(6H)-one. After stirring for 10 min, the reaction was treated with 5 g (0.035 m) of CH3I and stirred an additional 45 min. Dilution with water to 250 ml and filtration gave 4.8 g (93%) of crude material. Crystallization from methanol/CH2Cl2 afforded pure material, mp 241°-243° C.

Workup

  1. stirringstirred an additional 45 min
  2. filtrationDilution with water to 250 ml and filtration

Sources & evidence

ORD record
ord-c10744a3adc243bea4940bfebd1ed598
Source dataset
uspto-grants-1976_11
Patent number
US03991064

Reaction notes

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