1H-Indole-3-propanoic acid → 1H-Indole-3-propanamide, N-methyl-

HRID 1702922Notes

Reaction equation

HRID 1702922 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][CH2:31][C:32]([OH:34])=O)=[CH:22]1.[CH3:35][NH2:36]>C(#N)C.N1C=CC=CC=1>[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][CH2:31][C:32]([NH:36][CH3:35])=[O:34])=[CH:22]1

Participants

7

Reactant 4

HCID 37441H-Indole-3-propanoic acidHCID 6329MethylamineHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydride

Product 1

HCID 76616991H-Indole-3-propanamide, N-methyl-

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent3×

Procedure

A mixture of 57 g trifluoroacetic acid and 105 g trifluoroacetic anhydride in 400 ml anhydrous acetonitrile are added dropwise to a stirred suspension of 95.1 g 3-(3-indolyl)propionic acid in 500 ml anhydrous acetonitrile and maintained with stirring at -15° for 30 minutes. Under good cooling 500 ml anhydrous pyridine are added between -20° and -15° and quickly 238 ml of a 4.2 N solution of anhydrous methylamine in acetonitrile. The mixture is warmed with stirring at 0° for 15 minutes and maintained to 0° for 3 hours. 3-(3-indolyl)-N-methyl-propionamide (M.pt 97°-98° after crystallization from methylene chloride/ethyl acetate) is obtained after working up.

Workup

  1. temperaturemaintained
  2. additionare added between -20° and -15°
  3. temperatureThe mixture is warmed
  4. stirringwith stirring at 0° for 15 minutes
  5. temperaturemaintained to 0° for 3 hours

Sources & evidence

ORD record
ord-44ebba0332634fb99e3376d1110cf41c
Source dataset
uspto-grants-1982_09
Patent number
US04350634

Reaction notes

Loading…