Methyl Acrylate → HCID 13233241, compound

HRID 1263266Notes

Reaction equation

HRID 1263266 reaction equation
Cl([O-])(=O)(=O)=O.[CH2:6]([CH:8]1[C:17]2[C:16]3[NH:18][C:19]4[C:24]([C:15]=3[CH2:14][CH2:13][N+:12]=2[CH2:11][CH2:10][CH2:9]1)=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=4)[CH3:7].[OH-].[Na+].[C:28]([O:32][CH3:33])(=[O:31])[CH:29]=[CH2:30]>ClCCl.O>[CH3:28][O-:31].[CH2:6]([C:8]1([CH2:30][CH2:29][C:28]([O:32][CH3:33])=[O:31])[C:17]2[C:16]3=[N:18][C:19]4[C:24]([CH:15]3[CH2:14][CH2:13][N+:12]=2[CH2:11][CH2:10][CH2:9]1)=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=4)[CH3:7]

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 14798Sodium HydroxideHCID 13139564HCID 13139564, compound

Product 1

HCID 13233241HCID 13233241, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

7.00 g. (16.2 mmoles) of 1-ethyl-9-bromo-1,2,3,4,6,7-hexahydro-12H-indolo[2,3-a]quinolizin-5-ium perchlorate are dissolved in 160 ml. of dichloromethane, the solution is poured into a separatory funnel, and the mixture of 28 ml. of a 10% aqueous sodium hydroxide solution and 111 ml. of water is added. The two-phase mixture is shaken thoroughly, the organic phase is separated, dried over anhydrous potassium carbonate, and filtered. 8.90 g. (103.5 mmoles) of methyl acrylate are added to the filtrate, which is a dichloro-methane solution of the free base. The resulting mixture is allowed to stand at room temperature for 2 days, thereafter the solvent is evaporated in vacuo, and the oily residue is crystallized from methanol. In this way 4.70 g. (64.5%) of 1-ethyl-1-(2'-methoxycarbonylethyl)-9-bromo-1,2,3,4,6,7-hexahydro-7aH-indolo[2,3-a]quinolizin-5-ium methoxide are obtained in the form of orange red crystals; m.p.: 140°-142° C. (from methanol).

Workup

  1. additionthe mixture of 28 ml
  2. customthe organic phase is separated
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. customthe solvent is evaporated in vacuo
  6. customthe oily residue is crystallized from methanol

Sources & evidence

ORD record
ord-ce9e82e995fb483c8db96b6cb23d6f95
Source dataset
uspto-grants-1984_06
Patent number
US04456607

Reaction notes

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