Dimethyl Sulfate → HCID 21445420, compound

HRID 597563Notes

Reaction equation

HRID 597563 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]1[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:5]2=1.[H-].[Na+].[CH3:22]OS(OC)(=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]1[N:13]([CH3:22])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:5]2=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 21445446HCID 21445446, compound

Product 1

HCID 21445420HCID 21445420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 14.3 g. of 2,6-dichloro-7H-indolo[2,3-c]-quinoline in 500 ml. of tetrahydrofuran was added 2.5 g. of a 57 percent dispersion of sodium hydride in oil and 5.0 ml. of dimethylsulfate. The mixture was stirred at room temperature overnight. The initially clear solution soon deposited the product as a colorless amorphous precipitate. The solid was collected and washed with water and tetrahydrofuran. After recrystallizations from acetonitrile, 14.5 g. (98 percent) colorless fibrous needles of 2,6-dichloro-7-methylindolo[2,3-c]-quinoline were obtained, which had a melting point of 226°-227°.

Workup

  1. customThe solid was collected
  2. washwashed with water and tetrahydrofuran
  3. customAfter recrystallizations from acetonitrile, 14.5 g

Sources & evidence

ORD record
ord-56f346bfd6fc463893758699866688d1
Source dataset
uspto-grants-1977_03
Patent number
US04014883

Reaction notes

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