Water → 1-[2-(Cyclobutylcarbonyl)aminophenyl]indoline

HRID 2052695Notes

Reaction equation

HRID 2052695 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH:25]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26]1.O>C(Cl)Cl>[CH:25]1([C:29]([NH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[O:30])[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 125191192-(2,3-dihydro-1H-indol-1-yl)aniline hydrochloride

Product 1

HCID 203763231-[2-(Cyclobutylcarbonyl)aminophenyl]indoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A slurry of 1-(2-aminophenyl)indoline hydrochloride (41.44 g) in CH2Cl2 (400 ml) under N2 at 0° C. is treated dropwise with a solution of triethylamine (2.2 equivalents) in CH2Cl2 (80 ml) and then with a solution of cyclobutylcarbonyl chloride (20 g) in CH2Cl2 (50 ml). After warming to room temperature, the product is poured into water (300 ml). The organic layer is washed with 4 N HCl, 2.5 N NaOH, water, dried (Na2SO4), filtered, and concentrated to yield 1-[2-(cyclobutylcarbonyl)aminophenyl]indoline, m.p. 81°-83.5° C.

Workup

  1. washThe organic layer is washed with 4 N HCl, 2.5 N NaOH, water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3af5af1cb54e4b099b99ccc5acaf017c
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

Loading…