Hydrochloric Acid → 5-Chloro-1-nitrosoindoline

HRID 267232Notes

Reaction equation

HRID 267232 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.Cl.[N:12]([O-])=[O:13].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:12]=[O:13])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1175965-ChloroindolineHCID 23668193Sodium Nitrite

Product 1

HCID 215559775-Chloro-1-nitrosoindoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 77 g. (0.5 mole) of 5-chloroindoline, 80 ml. of concentrated hydrochloride acid and 500 ml. of crushed ice was stirred while a solution of 35 g. of sodium nitrite in 100 ml. of water was added over five minutes. The temperature was kept between 10°C. to 15°C. by addition of ice. The mixture was stirred for 1 hour and then filtered. Recrystallization of the product from benzene-isooctane gave 57 g. (68%) of product which melted at 120°-122°C.

Workup

  1. additionA mixture of 77 g
  2. additionThe temperature was kept between 10°C. to 15°C. by addition of ice
  3. stirringThe mixture was stirred for 1 hour
  4. filtrationfiltered
  5. customRecrystallization of the product from benzene-isooctane
  6. customgave 57 g

Sources & evidence

ORD record
ord-453428b0b93c4e798632b3a4785e6c7f
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

Loading…