Ammonia → 4,5-Dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carboxamide

HRID 1447426Notes

Reaction equation

HRID 1447426 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]([O:18]CC)=O)=[CH:13][C:14](=[O:15])[C:3]1=2.[NH3:21]>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]([NH2:21])=[O:18])=[CH:13][C:14](=[O:15])[C:3]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12620579HCID 12620579, compound

Product 1

HCID 126284154,5-Dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 11.0 g (40.7 mmole) of ethyl 4,5-dihydro-5-methyl-4-oxopyrano[3,2-b]indole-2-carboxylate in 500 ml ethanol was stirred in ice while gaseous ammonia was added until the reaction mixture temperature reached 20° C. (ca. 10 min). The ice bath was removed, and stirring at room temperature was continued for a total of 24 hr. The light yellow solid was filtered and washed with a little cold ethanol. Recrystallization from 50% aqueous DMF gave light yellow needles of mp >295° C.

Workup

  1. additionwas added until the reaction mixture temperature
  2. customreached 20° C.
  3. custom(ca. 10 min)
  4. customThe ice bath was removed
  5. customwas continued for a total of 24 hr
  6. filtrationThe light yellow solid was filtered
  7. washwashed with a little cold ethanol
  8. customRecrystallization from 50% aqueous DMF
  9. customgave light yellow needles of mp >295° C.

Sources & evidence

ORD record
ord-7d532ecea47549c4bb60c6133f75d114
Source dataset
uspto-grants-1982_02
Patent number
US04316904

Reaction notes

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