Ammonia → HCID 13408307, compound

HRID 543204Notes

Reaction equation

HRID 543204 reaction equation
[Na].N.[NH2-].[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[CH:16]=3)=[CH:9][CH:8]=1.[CH3:24]I>O1CCCC1>[CH3:24][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:22][CH3:23])[CH:16]=2)[CH:21]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([O:6][CH3:5])=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6328Methyl iodideHCID 24533Sodium amideHCID 5360545SodiumHCID 123989986-Methoxy-2-(4-methoxyphenyl)-1H-indole

Product 1

HCID 13408307HCID 13408307, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

There were added in portions 0.06 gram atom of sodium to 200 ml of liquid ammonia. At -70° C. there were dropped into the sodamide solution a solution of 8.85 grams (35 mmol) of 2-(4-methoxy-phenyl)-6-methoxy-indole in 100 ml of absolute tetrahydrofuran, stirring continued for one half hour and then there were dropped in 6 grams (42 mmol) of methyl iodide in 30 ml of absolute tetrahydrofuran. After a further 30 minutes there was removed the cold bath and the ammonia allowed to vaporize overnight. The residue was treated carefully with water and then extracted with ether. The organic phase was washed, dried, and the solvent removed on a rotary evaporator. The residue is recrystallized from ethanol. Yield: 8.63 grams, M.P. 163°-166° C.

Workup

  1. waitcontinued for one half hour
  2. customAfter a further 30 minutes there was removed the cold bath
  3. additionThe residue was treated carefully with water
  4. extractionextracted with ether
  5. washThe organic phase was washed
  6. customdried
  7. customthe solvent removed on a rotary evaporator
  8. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-3266296b429a46c79e9745841d593c6a
Source dataset
uspto-grants-1987_04
Patent number
US04661511

Reaction notes

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