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Hydrochloric Acid → 4-(5,6-Dimethoxyindolinyl)-phenylamine hydrochloride

HRID 1582502
Notes
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Reaction equation

HRID 1582502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[CH2:7][CH2:6]2.[H][H].[ClH:25]>C(O)C.O.[Pd]>[ClH:25].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH2:7][CH2:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 227173945,6-Dimethoxy-1-(4-nitrophenyl)-indolineHCID 178418361HCID 178418361, compound

Product 1

HCID 227173894-(5,6-Dimethoxyindolinyl)-phenylamine hydrochlorideYield 84.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 19096565
Water ethanol
Solvent

Procedure

5,6-Dimethoxy-1-(4-nitrophenyl)-indoline was hyrogenated overnight with Pd (5%) on carbon in ethanol/water (8:2) in a shaking “duck”. When the uptake of hydrogen had come to an end, 10% hydrochloric acid was added, the catalyst was filtered off and the remainder was concentrated to dryness. The residue was dried in vacuo at 45° C. The product 4-(5,6-dimethoxyindolinyl)-phenylamine hydrochloride was obtained in a yield of 84.9% (melting point: 143-145° C.).

Workup

  1. additionwas added
  2. filtrationthe catalyst was filtered off
  3. concentrationthe remainder was concentrated to dryness
  4. customThe residue was dried in vacuo at 45° C

Sources & evidence

ORD record
ord-eb46486808cf46909edccb043d22ec51
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06736862B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes