Hydrochloric Acid → HCID 13006976, compound

HRID 381192Notes

Reaction equation

HRID 381192 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][N:10]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[CH:11]1.CC(C)([O-])C.[K+].Cl>CC(O)(C)C>[CH3:9][N:10]1[C:18]2[CH:17]=[CH:16][C:15]([CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[C:14]([OH:19])[C:13]=2[CH:12]=[CH:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 103713-PyridinecarboxaldehydeHCID 2802261-Methyl-1,5,6,7-tetrahydro-4H-indol-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 13006976HCID 13006976, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

500 cm3 of 2-methyl-2-propanol, 75 g of pyridine-3-carboxaldehyde and 100 g of 1-methyl-1,5,6,7-tetrahydroindol-4-one were introduced into a 1-liter reactor equipped with a mechanical stirrer and surmounted by a condenser and a thermometer. After 10 minutes of stirring, 157 g of potassium tert-butoxide were added in small portions over 15 minutes. Following addition, the temperature was held at 75° C. for 1 hour. The reaction mixture was allowed to return to room temperature and then was neutralized (pH=6) with 20% hydrochloric acid. It was poured into 2 kg of ice-water. The precipitate obtained was filtered off with suction and washed with diisopropyl ether and with petroleum ether. It was dried over potash under vacuum at 30° C. This gave 120 g of 1-methyl-5-pyridin-3-ylmethyl-1H-indol-4-ol with a yield of 74%.

Workup

  1. customequipped with a mechanical stirrer
  2. customsurmounted by a condenser
  3. additionaddition
  4. waitthe temperature was held at 75° C. for 1 hour
  5. customto return to room temperature
  6. customThe precipitate obtained
  7. filtrationwas filtered off with suction
  8. washwashed with diisopropyl ether and with petroleum ether
  9. dry with materialIt was dried over potash under vacuum at 30° C

Sources & evidence

ORD record
ord-94f1e84a7bb14c41ab945327b777878d
Source dataset
uspto-grants-2001_10
Patent number
US06306181B1

Reaction notes

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