4-Chlorobenzoyl chloride → HCID 12940208, compound

HRID 1659636Notes

Reaction equation

HRID 1659636 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.[OH-].[Na+].[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[ClH:22].[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:1][CH:2]2[CH2:11][CH:10]3[N:5]([CH2:6][CH2:7][C:8]4[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=43)[CH2:4][CH2:3]2)=[O:28])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940208HCID 12940208, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (8 g, 0.03 mole), 200 ml of toluene and 80 ml of 20% NaOH was cooled to 10° in an ice bath at which point 4-chlorobenzoyl chloride (5.5 g, 0.03 mole) was added dropwise with stirring. The mixture was stirred in the cold for 1 hour whereupon the solid was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol-chloroform (3:1:1) as eluant. The major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in 2-propanol-ethyl acetate and was recrystallized from methanol-ethyl acetate twice to yield 4.2 g of the desired product, m.p. (decomposed at 253°-4°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR23##

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred in the cold for 1 hour whereupon the solid
  3. filtrationwas collected by filtration
  4. customchromatographed over silica gel
  5. customwas recrystallized from methanol-ethyl acetate twice

Sources & evidence

ORD record
ord-56b9b645b20c420aa0a8ae41ddd29d4e
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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