Lithium Hydroxide → HCID 23369864, compound

HRID 1900611Notes

Reaction equation

HRID 1900611 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]CC)=[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].O.[OH-].[Li+].[OH-].[Li+].[Cl-].[Na+]>C1COCC1.C(O)(=O)C.O>[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]([OH:24])=[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

8

Reactant 4

HCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 23369861HCID 23369861, compound

Product 1

HCID 23369864HCID 23369864, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-cyano-9-hydroxy-4-(3-nitrophenyl)-2-(1-pyrrolyl)-4H-naphtho[1,2-b]pyran-8-carboxylate (1.91 g) was dissolved in THF (10 ml). Water (1 ml) and lithium hydroxide monohydrate (180 mg) were added and the solution stirred at room temperature for 45 minutes. A further quantity of lithium hydroxide (180 mg) was added and the solution heated under reflux for one hour. The solution was poured into water (100 ml) and glacial acetic acid (50 ml) added. Solid sodium chloride was added until no more would dissolve, then the mixture extracted with ethyl acetate (3×200 ml). The combined organic extracts were dried over magnesium sulphate, then solvent removed under reduced pressure to give a brown-yellow solid. This was triturated with ether (10 ml), the solid collected by filtration and dried to yield 3-cyano-9-hydroxy-4-(3-nitrophenyl)-2-(1-pyrrolyl)-4H-naphtho[1,2-b]pyran-8-carboxylic acid, m.p. >230° C.

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for one hour
  3. additionadded
  4. dissolutionwould dissolve
  5. extractionthe mixture extracted with ethyl acetate (3×200 ml)
  6. dry with materialThe combined organic extracts were dried over magnesium sulphate
  7. customsolvent removed under reduced pressure
  8. customto give a brown-yellow solid
  9. customThis was triturated with ether (10 ml)
  10. filtrationthe solid collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-d1e90301433340789718eae844b9bae3
Source dataset
uspto-grants-1996_11
Patent number
US05576325

Reaction notes

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