Hydrochloric Acid → HCID 69058882, compound

HRID 730410Notes

Reaction equation

HRID 730410 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[CH:9][C:10]=2[CH3:12])[N:5]([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)[C:4]=1/[CH:24]=[CH:25]/[C:26]([O:28]CC)=[O:27])#[N:2].C1(C)C=CC=CC=1.[OH-].[Na+].Cl>O1CCCC1.O>[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[CH:9][C:10]=2[CH3:12])[N:5]([CH:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)[C:4]=1/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 86606792HCID 86606792, compound

Product 1

HCID 69058882HCID 69058882, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl (E)-3-[3-cyano-4,6-dimethyl-1-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-propenoate (1.2 g, 3 mmol) in tetrahydrofuran (6 ml)-toluene (6 ml) was heated to 50° C. To the resultant solution was added a 2 N aqueous sodium hydroxide solution (4 ml, 8 mmol) and the mixture was stirred at 50° C. for 20 minutes. Then, water (100 ml) was added to the reaction mixture, which was adjusted to pH 3 to 4 with 12 N hydrochloric acid, and then the product was extracted using ethyl acetate-tetrahydrofuran (3:1, v/v). The organic extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum. Hexane was added to the residue on a solid material and the residue was finely crushed using a spatula. The solid was collected by filtration using Kiriyama Roht and was washed with hexane to give the title compound (yield (amount) 1.0 g, yield (rate) 92%).

Workup

  1. extractionthe product was extracted
  2. extractionThe organic extract
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under vacuum
  6. additionHexane was added to the residue on a solid material
  7. customthe residue was finely crushed
  8. filtrationThe solid was collected by filtration
  9. washwas washed with hexane

Sources & evidence

ORD record
ord-72e2be67fa7b4d389c81634a77b90de2
Source dataset
uspto-grants-2009_09
Patent number
US07582651B2

Reaction notes

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