Chloroacetamide → 10-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine-2-acetamide

HRID 261731Notes

Reaction equation

HRID 261731 reaction equation
Cl[CH2:2][C:3]([NH2:5])=[O:4].[OH:6][C:7]1[C:12]2[C:13]3[CH2:14][NH:15][CH2:16][CH2:17][C:18]=3[C:19]([CH3:22])([CH3:21])[O:20][C:11]=2[CH:10]=[C:9]([CH:23]([CH3:31])[CH:24]([CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]=1.C(N(CC)CC)C>CN(C)C=O>[OH:6][C:7]1[C:12]2[C:13]3[CH2:14][N:15]([CH2:2][C:3]([NH2:5])=[O:4])[CH2:16][CH2:17][C:18]=3[C:19]([CH3:21])([CH3:22])[O:20][C:11]=2[CH:10]=[C:9]([CH:23]([CH3:31])[CH:24]([CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:8]=1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 8471TriethylamineHCID 2135435H-(1)Benzopyrano(4,3-c)pyridine, 1,2,3,4-tetrahydro-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-

Product 1

HCID 2132113810-Hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine-2-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.03 g (0.011 mole) of 2-chloroacetamide in 8 ml of dimethylformamide was added dropwise to a stirred solution of 3.57 g (0.01 mole) of 10-hydroxy-5,5-dimethyl-8-(1,2-dimethylheptyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine in 12 ml of dimethylformamide and 1.11 g (0.011 mole) of triethylamine. After stirring for 17 hours, the mixture was diluted with 20 ml. of water and extracted with ether. The combined ether extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was recrystallized from acetonitrile, m.p. 165°-168°.

Workup

  1. additionthe mixture was diluted with 20 ml
  2. extractionof water and extracted with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from acetonitrile, m.p. 165°-168°

Sources & evidence

ORD record
ord-2d78b87b313a4731bf0a3aba2c2ff434
Source dataset
uspto-grants-1979_05
Patent number
US04152327

Reaction notes

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