3,4-Dichlorobenzoic acid → HCID 12940206, compound

HRID 1659635Notes

Reaction equation

HRID 1659635 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=O.O=S(Cl)Cl.[NH2:16][CH:17]1[CH2:26][CH:25]2[N:20]([CH2:21][CH2:22][C:23]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:24]=32)[CH2:19][CH2:18]1>C1(C)C=CC=CC=1.[OH-].[Na+]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:16][CH:17]1[CH2:26][CH:25]2[N:20]([CH2:21][CH2:22][C:23]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[CH:27][C:24]=32)[CH2:19][CH2:18]1)=[O:7]

Participants

6

Reactant 3

HCID 58173,4-Dichlorobenzoic acidHCID 24386Thionyl ChlorideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940206HCID 12940206, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3,4-dichlorobenzoic acid (6.5 g) and 25 ml of SOCl2 were refluxed for 3 hours and concentrated in vacuo. The concentrate was dissolved in 10 ml of toluene and added dropwise to a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (8 g, 0.03 mole) in 200 ml of toluene and 75 ml of 20% NaOH. The mixture was stirred in the cold for 1 hour whereupon the solid material was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol-chloroform (7:2:1) as eluant. This major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and methanol, isolated by evaporation of the solvent and recrystallized from methanol-ethyl acetate to yield 3.8 g of the desired product, m.p. (decomposed at 271°-3°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR22##

Workup

  1. temperaturewere refluxed for 3 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe concentrate was dissolved in 10 ml of toluene
  4. filtrationwas collected by filtration
  5. customchromatographed over silica gel
  6. customisolated by evaporation of the solvent
  7. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-159e0077c2df4cfcab2b15c219e9bc92
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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