Hydrochloric Acid → HCID 12519121, compound

HRID 2052690Notes

Reaction equation

HRID 2052690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-])=O)[CH2:6][CH2:5]2.Cl>C(O)C.CCOCC>[ClH:1].[NH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12519117HCID 12519117, compound

Product 1

HCID 12519121HCID 12519121, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 13.7 g of 5-chloro-1-(2-nitrophenyl)indoline and 0.25 g of 1% Pt on C in 250 ml absolute ethanol is shaken at 50 psi of H2 until the theoretical amount of H2 is taken up. The mixture is filtered and the solvent removed at 50° C. to leave the product base as an oil. This is dissolved in 200 ml of ether, cooled to 0° C., and treated with gaseous HCl to precipitate 1-(2-aminophenyl)-5-chloroindoline hydrochloride, m.p. 235°-238° C. dec.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent removed at 50° C.
  3. customto leave the product base as an oil
  4. customto precipitate 1-(2-aminophenyl)-5-chloroindoline hydrochloride, m.p. 235°-238° C. dec.

Sources & evidence

ORD record
ord-e995a0714d5b468693934fe28c22bf5d
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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