1-Acetyl-5-(N,N-dimethylamino)indoline → N,N-Dimethylindolin-5-amine

HRID 356016Notes

Reaction equation

HRID 356016 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13]([CH3:15])[CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C>Cl>[CH3:15][N:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH2:5][CH2:6]2)[CH3:14]

Participants

3

Reactant 1

HCID 189409071-Acetyl-5-(N,N-dimethylamino)indoline

Product 1

HCID 16767807N,N-Dimethylindolin-5-amineYield 61%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-Acetyl-5-(N,N-dimethylamino)indoline (D12) (0.6 g, 2.94 mmol) in conc. HCl (0.6 ml) was heated over a steam bath for 45 min. The mixture was partitioned between sat aq. K2CO3 (50 ml) and CHCl3 (50 ml) the organic solution dried (Na2SO4), evaporated to dryness under reduced pressure and purified by column chromatography (SiO2, EtOAc/MeOH 5-10%) to afford the title compound (290 mg, 61%) which was used directly in Example 4.

Workup

  1. customThe mixture was partitioned
  2. dry with materialdried (Na2SO4)
  3. customevaporated to dryness under reduced pressure
  4. custompurified by column chromatography (SiO2, EtOAc/MeOH 5-10%)

Sources & evidence

ORD record
ord-afa788553e494ae9bb4bbeb0f9499f89
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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