2-Methoxybenzoyl chloride → HCID 12940216, compound

HRID 1659638Notes

Reaction equation

HRID 1659638 reaction equation
[NH2:1][CH:2]1[CH2:11][CH:10]2[N:5]([CH2:6][CH2:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=32)[CH2:4][CH2:3]1.[C:20]([Cl:30])(=[O:29])[C:21]1[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>C1(C)C=CC=CC=1.[OH-].[Na+]>[ClH:30].[CH3:17][O:16][C:14]1[C:13]([O:18][CH3:19])=[CH:12][C:9]2[CH:10]3[N:5]([CH2:6][CH2:7][C:8]=2[CH:15]=1)[CH2:4][CH2:3][CH:2]([NH:1][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH3:28])[CH2:11]3

Participants

5

Reactant 2

HCID 889692-Methoxybenzoyl chlorideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940216HCID 12940216, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine, (7 g, 0.026 mole) in 200 ml of toluene and 75 ml of 20% NaOH, was added dropwise 4.8 g of 2-anisoyl chloride in toluene. The mixture was stirred in the cold for 1 hour after which the toluene layer was collected, dried over MgSO4 and concentrated in vacuo. The concentrate was chromatographed over silica gel using ethyl acetate-methanol (4:1) as eluant. The major fraction (6.5 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and the mixture concentrated by removal of the solvent in vacuo. The salt was crystallized from acetone and twice recrystallized from methanol-ethyl acetate to yield 3.0 g of the desired product, m.p. (decomposed at 243°-4°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR27##

Workup

  1. customwas collected
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe concentrate was chromatographed over silica gel
  5. concentrationthe mixture concentrated by removal of the solvent in vacuo
  6. customThe salt was crystallized from acetone
  7. customtwice recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-09ace13f58ce414b9ce910c0b47d1134
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

Loading…