HCID 19101008, compound → HCID 19101031, compound

HRID 1975222Notes

Reaction equation

HRID 1975222 reaction equation
[C:1]([N:4](C(=O)C)[C:5]1[O:10][C:9]2[C:11]3[C:16]([CH:17]=[CH:18][C:8]=2[CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:6]=1[C:28]#[N:29])=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:3])[CH3:2]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[O:10][CH:9]2[C:11]3[C:16]([CH:17]=[CH:18][C:8]2=[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:6]=1[C:28]#[N:29])=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 19101008HCID 19101008, compound

Product 1

HCID 19101031HCID 19101031, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Diacetylamino-4-(3-nitrophenyl)-4H-naphtho[1,2-b]pyran-3-carbonitrile (3.62 g) was dissolved in chloroform (200 ml) and mechanically stirred in the presence of Grade III alumina (36 g) for 24 hours at ambient temperature. The suspension was filtered, the alumina pad was washed through with 5% methanol in chloroform, the combined filtrates were evaporated and the residue was triturated with a little chloroform. The white solid was dissolved in dioxan (50 ml) and left to stand for 24 hours. An impurity precipitated out and this was filtered off. Water was added (200 ml) to the filtrate and the solid produced was filtered off, washed with water and dried. This solid was passed through a chloroform--`flash` silica column. The fractions containing product were bulked, evaporated to dryness and triturated with methanol to give yellow crystals of 2-acetamido-4-(3-nitrophenyl)-naphtho[1,2-b]pyran-3-carbonitrile, m.p. 234.5°-236° C.

Workup

  1. filtrationThe suspension was filtered
  2. washthe alumina pad was washed through with 5% methanol in chloroform
  3. customthe combined filtrates were evaporated
  4. customthe residue was triturated with a little chloroform
  5. dissolutionThe white solid was dissolved in dioxan (50 ml)
  6. waitleft
  7. customAn impurity precipitated out
  8. filtrationthis was filtered off
  9. additionWater was added (200 ml) to the filtrate
  10. customthe solid produced
  11. filtrationwas filtered off
  12. washwashed with water
  13. customdried
  14. additionThe fractions containing product
  15. customevaporated to dryness
  16. customtriturated with methanol

Sources & evidence

ORD record
ord-ea97e92a1fc44bb6a746d18a7b5e9885
Source dataset
uspto-grants-1994_02
Patent number
US05284868

Reaction notes

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