Acetic Acid → HCID 19085798, compound

HRID 962641Notes

Reaction equation

HRID 962641 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:16]3[CH2:15][CH2:14][NH:13][CH2:12][C:11]=3[C:10](=[O:17])[O:9][C:7]=2[CH:8]=1.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH:28]=O)=[CH:20][CH:19]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[NH4+]>ClCCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:16]3[CH2:15][CH2:14][N:13]([CH2:28][C:21]4[C:22]5[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:18]=[CH:19][CH:20]=4)[CH2:12][C:11]=3[C:10](=[O:17])[O:9][C:7]=2[CH:8]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 780724-QuinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 19085798HCID 19085798, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A mixture of 8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one (1.0 g, 4.3 mmol), 4-quinolinecarboxaldehyde (0.68 g, 4.3 mmol), and glacial acetic acid (1.75 mL, 30.6 mmol) in 20 mL of 1,2-dichloroethane is treated in small portions with sodium triacetoxyborohydride (1.3 g, 6.1 mmol). The mixture is stirred at room temperature for 24 hours. Water (100 mL) is slowly added, followed by concentrated ammonium hydroxide until slight basicity. The mixture is extracted with dichloromethane, and the combined organic layers are washed with brine, dried (anhydrous sodium sulfate), and evaporated. Purification of the residue by flash chromatography (silica gel, 3% methanol in dichloromethane elution) gives 0.70 g (42%) of product; mp 186°-188° C.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe combined organic layers are washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated
  5. customPurification of the residue
  6. washby flash chromatography (silica gel, 3% methanol in dichloromethane elution)

Sources & evidence

ORD record
ord-ff2131346ed54d26ade260c46c5533eb
Source dataset
uspto-grants-1998_06
Patent number
US05760050

Reaction notes

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