Ammonia → 5-Ethyl-2-(1-hydroxy-ethyl)-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 1181576Notes

Reaction equation

HRID 1181576 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[N:7]([CH2:12][CH3:13])[C:6](=[O:14])[C:5]2([CH3:16])[CH3:15].[OH:17][CH:18]([CH3:22])[C:19](O)=O.N>Cl>[CH2:12]([N:7]1[C:8]2[CH:9]=[C:10]3[N:11]=[C:19]([CH:18]([OH:17])[CH3:22])[NH:1][C:2]3=[CH:3][C:4]=2[C:5]([CH3:15])([CH3:16])[C:6]1=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 612Lactic AcidHCID 674257515,6-Diamino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 694023135-Ethyl-2-(1-hydroxy-ethyl)-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-oneYield 97.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 5,6-diamino-1-ethyl-3,3-dimethyl-1,3-dihydro-indol-2-one (10 g, 46 mmol), 2-hydroxy-propionic acid (9.13 g, 91.2 mmol) in HCl (100 mL, 4N) was refluxed for 16 h. After cooling, neutralization with aqueous ammonia (25%) and stirring for 1.5 h the precipitate was filtered and dried in vacuo at 50° C. yielding 12.29 g (95%) of a grey solid.

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationwas filtered
  3. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-5cb506c6400e43b1a248b25a3f03bb31
Source dataset
uspto-grants-2007_10
Patent number
US07285569B2

Reaction notes

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