Acetic Acid → HCID 10640530, compound

HRID 962633Notes

Reaction equation

HRID 962633 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.[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.CN1CCN(C)C1=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:16]3[CH2:15][CH2:14][N:13]([CH2:18][C:19]4[CH:26]=[CH:25][C:22]([CH3:23])=[CH:21][CH:20]=4)[CH2:12][C:11]=3[C:10](=[O:17])[O:9][C:7]=2[CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 77254-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 10640530HCID 10640530, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one (1.2 g, 5.2 mmol) and 4-methylbenzaldehyde (0.68 g, 5.7 mmol) in 20 mL of tetrahydrofuran and 7 mL of 1,3-dimethyl-2-imidazolidinone is treated with glacial acetic acid (0.29 mL, 5.2 mmol). The mixture is stirred for 10 minutes, and then sodium triacetoxyborohydride (1.6 g, 7.5 mmol) is added in portions over 30 minutes. The mixture is stirred for 16 hours, then added to 300 mL of ice water. The precipitated solid is filtered, washed with water, and recrystallized from ethyl acetate to yield 1.2 g (70%) of product, mp 147°-149° C.

Workup

  1. stirringThe mixture is stirred for 16 hours
  2. filtrationThe precipitated solid is filtered
  3. washwashed with water
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d63db3005a9f4d7887cbda3a20b870ee
Source dataset
uspto-grants-1998_06
Patent number
US05760050

Reaction notes

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