Hydrochloric Acid → HCID 86729746, compound

HRID 2272586Notes

Reaction equation

HRID 2272586 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH2:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].C[Al](C)C.[C:21]1(=[O:27])[O:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][OH:27])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85883-Amino-9-ethylcarbazoleHCID 10953Delta-ValerolactoneHCID 16682925Trimethylaluminum

Product 1

HCID 86729746HCID 86729746, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 9-ethyl-9H-carbazol-3-amine (300 mg, 1.43 mmol) in toluene (4 mL) was added trimethylaluminium (1.8M in toluene solution, 1.189 mL, 2.14 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added a solution of δ-valerolactone (0.129 mL, 1.43 mmol) in toluene (4 mL) at room temperature, and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was cooled to 0° C., neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure to give N-(9-ethyl-9H-carbazol-3-yl)-5-hydroxypentanamide (420 mg, 1.352 mmol, 95%) as a pale-yellow powder.

Workup

  1. stirringthe mixture was stirred at 80° C. for 4 hr
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-25ed18c0044849cb9f765a6a901a1ffc
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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