Pyridine → 2-[2-(Octyloxycarbonylamino)phenyl]-2,3-dihydro-1H-indole

HRID 249332Notes

Reaction equation

HRID 249332 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:3].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21]1.N1C=CC=CC=1>C(Cl)Cl>[CH2:5]([O:4][C:2]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21]1)=[O:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81956Carbonochloridic acid, octyl esterHCID 197614202-(2-Aminophenyl)-2,3-dihydro-1H-indole

Product 1

HCID 197614132-[2-(Octyloxycarbonylamino)phenyl]-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Octyl chloroformate (2.00 ml) was added dropwise to a solution of 2.15 g 2-(2-aminophenyl)-2,3-dihydro-1H-indole and 2.00 ml pyridine in 35 ml CH2Cl2 at 0° C. The solution was stirred five hours at 0° C. and then quenched with water. The organic layer was separated, washed with 5% HCl and saturated NaCl solution, dried (MgSO4), and concentrated to yield a solid. Purification by flash chromatography using CH2Cl2 /hexane (1:2) as eluent gave 1.74 g solid, m.p. 99°-102° C.

Workup

  1. customquenched with water
  2. customThe organic layer was separated
  3. washwashed with 5% HCl and saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto yield a solid
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-783e13f337c74e3eacd77cdfc62a8bcc
Source dataset
uspto-grants-1993_05
Patent number
US05214059

Reaction notes

Loading…