Sodium Hydroxide → HCID 15027721, compound

HRID 345964Notes

Reaction equation

HRID 345964 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:11][C:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:17](=O)[N:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15]=2[S:14][C:13]=1[C:32]([O:34][CH3:35])=[O:33].[OH-].[Na+]>O1CCCC1.CCOCC>[NH2:11][C:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:17][N:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:15]=2[S:14][C:13]=1[C:32]([O:34][CH3:35])=[O:33]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 9841326HCID 9841326, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15027721HCID 15027721, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.34 g of lithium aluminum hydride in 30 ml of tetrahydrofuran was added a solution of 1.20 g aluminium chloride in 60 ml of ether for 10 minutes. To the mixture was added a solution of 1.05 g of methyl 1-amino-4,5-dihydro-5-oxo-4-phenyl-thieno[2,3-c]isoquinoline-2-carboxylate in 60 ml of tetrahydrofuran for 50 minutes, which was prepared by Example 1, and the mixture was stirred for 40 minutes. To the reaction mixture was added 30 ml of a 5% sodium hydroxide aqueous solution, and the mixture was stirred. The aqueous layer was extracted with 30 ml of tetrahydrofuran twice. The organic layers were combined together, and dried over anhydrous magnesium sulfate. The dried solution was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/chloroform=1/1) to obtain amorphous product in orange-yellow. The amorphous product obtained was triturated with n-hexane to obtain 180 mg of the desired product.

Workup

  1. customwhich was prepared by Example 1
  2. stirringthe mixture was stirred
  3. extractionThe aqueous layer was extracted with 30 ml of tetrahydrofuran twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe dried solution was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/chloroform=1/1)
  7. customto obtain amorphous product in orange-yellow
  8. customThe amorphous product obtained
  9. customwas triturated with n-hexane

Sources & evidence

ORD record
ord-0d4331ab167741a4b294f0c3c86b0442
Source dataset
uspto-grants-1991_10
Patent number
US05059692

Reaction notes

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