Potassium Carbonate → HCID 59300791, compound

HRID 2235370Notes

Reaction equation

HRID 2235370 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].Br[CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>Cl>[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]([CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 59300791HCID 59300791, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1.49 g) is alkylated using (3-bromo-propoxymethyl)-benzene (1,36 g; 5.95 mmol) and K2CO3 (2.07 g; 15.0 mmol) at RT for 16 h. After aqueous work-up the crude material is de-acetylated in hydrochloric acid (6 N, 60 ml) at reflux. After aqueous work-up 5-amino-1-(3-benzyloxy-propyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (2.1 g) is obtained and used without further purification.

Workup

  1. customat RT
  2. customfor 16 h
  3. temperatureat reflux

Sources & evidence

ORD record
ord-b8144806dfaa4f3291291c9847f701d6
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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