Potassium Carbonate → HCID 59300726, compound

HRID 2235348Notes

Reaction equation

HRID 2235348 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300726HCID 59300726, compound

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1.5 g) is synthesized according to the general procedure using 4-methoxybenzyl chloride (0.92 g; 5.86 mmol) and K2CO3 (2.3 g; 16.6 mmol) at RT for 20 h. After filtration and evaporation of the solvent the crude material is de-acetylated under reflux conditions in 2-propanol (15 ml) and hydrochloric acid (6 N; 45 ml). Pure 5-amino-1-(4-methoxy-benzyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (1.71 g) precipitates by pouring the reaction mixture into ice-water.

Workup

  1. customat RT
  2. customfor 20 h
  3. filtrationAfter filtration and evaporation of the solvent the crude material
  4. customPure 5-amino-1-(4-methoxy-benzyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (1.71 g) precipitates
  5. additionby pouring the reaction mixture into ice-water

Sources & evidence

ORD record
ord-4c36e2e3055b40b58e9ad20e1de3c970
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…