Ammonia → HCID 12740033, compound

HRID 648122Notes

Reaction equation

HRID 648122 reaction equation
N.[Na].[CH3:3][O:4][C:5]1[C:6]2[CH:19]=[C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:16][C:7]=2[CH2:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[CH:11]=1.[CH3:25]I.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1.O.CCOCC>[CH3:3][O:4][C:5]1[C:6]2[CH:19]=[C:18]([CH:20]([CH3:25])[C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:16][C:7]=2[CH2:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[CH:11]=1

Participants

10

Reactant 6

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 12740032HCID 12740032, compound

Product 1

HCID 12740033HCID 12740033, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

Small pieces of ferric nitrate nonahydrate were added to 75 ml of liquid ammonia, and subsequently 0.733 g of metallic sodium was added little by little. The mixture was stirred for 30 minutes. To the stirred mixture was added dropwise over the course of 10 minutes a solution of 6.25 g of methyl 11-methoxy-5H-dibenzo[a,d]cyclohepten-2-acetate obtained in Example 12 in 12 ml of dry toluene. The mixture was stirred for 25 minutes, and a solution of 1.98 ml of methyl iodide in 2 ml of dry toluene was added dropwise over the course of 2 minutes. The mixture was further stirred for 1 hour, and then 1.83 g of ammonium chloride and 12 ml of toluene were added. Ammonia was released at room temperature. Then, 24 ml of 10% hydrochloric acid was added under ice cooling and stirring, and the mixture was stirred for 15 minutes. Ether (100 ml) and 100 ml of water were added to extract the solution. The organic layer was successively washed with water, a 10% aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was chromatographed on a silica gel column using benzene as an eluent. From the eluate, 5.91 g of methyl 2-(11-methoxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionate was obtained as a colorless oily substance.

Workup

  1. additionwas added little by little
  2. stirringThe mixture was stirred for 25 minutes
  3. stirringThe mixture was further stirred for 1 hour
  4. customwas released at room temperature
  5. stirringstirring
  6. stirringthe mixture was stirred for 15 minutes
  7. extractionto extract the solution
  8. washThe organic layer was successively washed with water
  9. dry with materiala 10% aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f33aac4ce2f24fe28aec056440252bd5
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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