Pyridine → 4,5-Dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carbonitrile

HRID 1447427Notes

Reaction equation

HRID 1447427 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[O:11][C:12]([C:16]([NH2:18])=O)=[CH:13][C:14](=[O:15])[C:3]1=2.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1>CN(C=O)C>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[O:11][C:12]([C:16]#[N:18])=[CH:13][C:14](=[O:15])[C:3]1=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 126284154,5-Dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carboxamide

Product 1

HCID 126284204,5-Dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.5 g (43.3 mmole) 4,5-dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carboxamide, 12.6 g (66.2 mmole) p-toluenesulfonyl chloride, and 10.3 g (10.5 ml, 130 mmole) of pyridine in 55 ml DMF was heated under nitrogen on a steam bath for 4 hr. The cooled mixture was added to 500 g ice/water, stirred for 20 min, and the pink solid was filtered and washed with cold water. Two recrystallizations from ethanol yielded light pink needles of mp 190°-192° C.

Workup

  1. temperaturewas heated under nitrogen on a steam bath for 4 hr
  2. filtrationthe pink solid was filtered
  3. washwashed with cold water
  4. customTwo recrystallizations from ethanol yielded light pink needles of mp 190°-192° C.

Sources & evidence

ORD record
ord-289a20c446844bb29efd9b52267322cf
Source dataset
uspto-grants-1982_02
Patent number
US04316904

Reaction notes

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