4-Nitrobenzoyl chloride → HCID 12940196, compound

HRID 1659632Notes

Reaction equation

HRID 1659632 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+].[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([Cl:31])=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C1(C)C=CC=CC=1>[ClH:31].[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:29](=[O:30])[C:28]1[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:33][CH:32]=1)[CH2:11]3

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940196HCID 12940196, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9, 10-dimethoxy-2H-benzo[a]quinolizine (7 g), 200 ml of toluene and 50 ml of 20% NaOH was cooled to below 10° and a solution of 4-nitrobenzoyl chloride (5 g) in toluene was added dropwise with stirring. The mixture was stirred in the cold for 1 hour and allowed to come to room temperature whereupon the solid was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol (6:1) as eluant. The major fraction (5.3 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and the solvent was removed in vacuo. The salt was crystallized from methanol-ether to yield 1.5 g of the desired product, m.p. (decomposed at 269°-70°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR17##

Workup

  1. temperaturewas cooled to below 10°
  2. stirringThe mixture was stirred in the cold for 1 hour
  3. customto come to room temperature whereupon the solid
  4. filtrationwas collected by filtration
  5. customchromatographed over silica gel
  6. customthe solvent was removed in vacuo
  7. customThe salt was crystallized from methanol-ether

Sources & evidence

ORD record
ord-a0a4ee39d7c1445581e82d11ec558e77
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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