Water → HCID 23369899, compound

HRID 1898936Notes

Reaction equation

HRID 1898936 reaction equation
[C:1]([C:3]1[CH:4]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:5]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([OH:27])=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=3)[C:6]=2[O:7][C:8]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)#[N:2].[C:37](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[C:1]([C:3]1[CH:4]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:5]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:37])=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=3)[C:6]=2[O:7][C:8]=1[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13]1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23369861HCID 23369861, compound

Product 1

HCID 23369899HCID 23369899, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-cyano-9-hydroxy-4-(3-nitrophenyl)-2-(1-pyrrolyl)-4H-naphtho[1,2-b]pyran-8-carboxylate (4 g) was dissolved in dry DMF (50 ml). Solid potassium carbonate (2.3 g) and methyl iodide (1.05 ml) were added and the mixture stirred at room temperature for 16 hours. The solution was poured into water (400 ml) and extracted with ethyl acetate (4×200 ml). The combined organic extracts were washed with water (2×250 ml), dried over magnesium sulphate, then solvent was removed under reduced pressure to yield a brown solid. This was triturated with ether (10 ml), the solid collected by filtration and dried to yield ethyl 3-cyano-9-methoxy-4-(3-nitrophenyl)-2-(1-pyrrolyl)-4H-naphtho[1,2-b]pyran-8-carboxylate as a dark yellow solid, m.p. 190°-191° C.

Workup

  1. extractionextracted with ethyl acetate (4×200 ml)
  2. washThe combined organic extracts were washed with water (2×250 ml)
  3. dry with materialdried over magnesium sulphate
  4. customsolvent was removed under reduced pressure
  5. customto yield a brown solid
  6. customThis was triturated with ether (10 ml)
  7. filtrationthe solid collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-0d6c7bec69254a77841ace900e9e4ce3
Source dataset
uspto-grants-1996_11
Patent number
US05571818

Reaction notes

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