Acetone → N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]acetamide

HRID 2052693Notes

Reaction equation

HRID 2052693 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.Cl.[CH3:18][C:19](C)=[O:20].C(Cl)(=O)C>C(N(CC)CC)C>[C:19]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)(=[O:20])[CH3:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 125191182-(2,3-Dihydro-1H-indol-1-YL)phenylamine

Product 1

HCID 12519125N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A stirred slurry, under N2, of 9.96 g of 1-(2-amino-phenyl)indoline.HCl and 300 ml of dry acetone is treated with 10.1 g of triethylamine over a 10 minute period. After cooling to 0°-5° C., 4.70 g of acetyl chloride is added dropwise over 0.5 hour. The mixture is stirred 18 hours at ambient temperature, then filtered. The filtrate is diluted with 100 ml of water and concentrated. When all the acetone is removed, the residue is filtered off, washed well with water, and dried to afford 1-(2-acetamidophenyl)indoline, m.p. 125°-128° C.

Workup

  1. temperatureAfter cooling to 0°-5° C.
  2. filtrationfiltered
  3. additionThe filtrate is diluted with 100 ml of water
  4. concentrationconcentrated
  5. customWhen all the acetone is removed
  6. filtrationthe residue is filtered off
  7. washwashed well with water
  8. customdried

Sources & evidence

ORD record
ord-4a3bb27f169a452e995c7bc951ea5edb
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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