Sodium Carbonate → HCID 54231420, compound

HRID 839585Notes

Reaction equation

HRID 839585 reaction equation
[C:1]([N:3]1[CH2:8][C:7]2[C:9]3[C:18]([OH:19])=[CH:17][C:16]([CH:20]([CH3:28])[CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][C:10]=3[O:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:30][OH:31].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:13][C:12]1([CH3:14])[C:6]2[CH2:5][CH2:4][N:3]([C:1](=[N:30][OH:31])[NH2:2])[CH2:8][C:7]=2[C:9]2[C:18]([OH:19])=[CH:17][C:16]([CH:20]([CH3:28])[CH:21]([CH3:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][C:10]=2[O:11]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20323749HCID 20323749, compound

Product 1

HCID 54231420HCID 54231420, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g (1.31 mmole) of 2-cyano-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 0.139 g (2.0 mmole) of hydroxylamine hydrochloride and 0.212 g (2.0 mmole) of sodium carbonate in 17 ml of dimethylformamide was heated on a steam bath for 1.5 hours. After cooling, the reaction mixture was partitioned between 50 ml each of chloroform and water. The organic layer was separated, washed with water, dried over Na2SO4 and filtered. After removal of the solvents on a rotary evaporator, the last traces of dimethylformamide were removed in vacuo. Crystallization from chloroform gave 280 mg (56%) of 5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine-2-carboxamidoxime as colorless crystals. Recrystallization of the compound from chloroform gave poor recovery (17.5%) of the crystalline material, m.p. 142°-45° C. The assigned structure was confirmed by the ir, nmr and mass spectra (M+ at 415). Thin-layer chromatography (20% methanol/chloroform on silica gel) revealed two spots corresponding to the two stereoisomers.

Workup

  1. temperaturewas heated on a steam bath for 1.5 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between 50 ml each of chloroform and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customAfter removal of the solvents
  9. customon a rotary evaporator
  10. customthe last traces of dimethylformamide were removed in vacuo
  11. customCrystallization from chloroform

Sources & evidence

ORD record
ord-91497536bdb04fe48c5d3744e7b07855
Source dataset
uspto-grants-1978_06
Patent number
US04096265

Reaction notes

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