N-Methylformanilide → HCID 23354002, compound

HRID 235265Notes

Reaction equation

HRID 235265 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:27](=[O:28])[CH:26]=[C:25]3[C:20]([C:21]4[CH:31]=[CH:30][S:29][C:22]=4[CH2:23][CH2:24]3)=[N:19]2)=[CH:14][CH:13]=1>O(Cl)Cl>[OH:10][CH2:9][C:30]1[S:29][C:22]2[CH2:23][CH2:24][C:25]3[C:20]([C:21]=2[CH:31]=1)=[N:19][N:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=1)[C:27](=[O:28])[CH:26]=3

Participants

4

Reactant 2

HCID 66737N-MethylformanilideHCID 10565743HCID 10565743, compound

Product 1

HCID 23354002HCID 23354002, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 24646Chlorine monoxideSolvent

Procedure

A mixture of 1.9 g of N-methylformanilide in 1.3 ml of phosphrus oxychloride was stirred at room temperature for an hour and 2.0 g of 2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin-3(2H)-one was added thereto. After stirring at room temperature for 10 hours, the mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in methanol and 1.0 g of sodium borohydride was added thereto under ice-cooling. After stirring for an hour, the mixture was poured into diluted hydrochloric acid and extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent. The solid was recrystallized from a mixed solvent of isopropyl alcohol and isopropyl ether to give 0.2 g of 8-hydroxymethyl-2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin3(2H)-one as a brown powder, melting at 166°-169° C.

Workup

  1. stirringAfter stirring at room temperature for 10 hours
  2. additionthe mixture was poured into ice-cold water
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in methanol
  8. addition1.0 g of sodium borohydride was added
  9. temperatureunder ice-cooling
  10. stirringAfter stirring for an hour
  11. additionthe mixture was poured into diluted hydrochloric acid
  12. extractionextracted with chloroform
  13. washThe extract was washed with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated in vacuo
  16. customThe residue was chromatographed on a silica gel column
  17. customThe solid was recrystallized from a mixed solvent of isopropyl alcohol and isopropyl ether

Sources & evidence

ORD record
ord-da69890833f74848ba00d2e4f68800f1
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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