Hydrochloric Acid → HCID 59293374, compound

HRID 1914603Notes

Reaction equation

HRID 1914603 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]2=[O:26].I[CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C(O)C.[OH-].[Na+].C(OCC)(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:28][CH3:29])[CH:16]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:14]2=[O:26]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 24953718HCID 24953718, compound

Product 1

HCID 59293374HCID 59293374, compoundYield 54%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 6-(2,3-dihydro-1H-inden-2-ylamino)-1,4-dihydro-4-oxo-1,5-naphthyridine-3-carboxylate (600 mg), iodoethane (1 g) and potassium carbonate (600 mg) were heated at 90° C. in DMF (20 ml) overnight. After a standard ethyl acetate/aqueous work-up, the residue from the evaporated organic layer (crude cyclized ethyl ester), was heated at 80° C. in a mixture of ethanol (25 ml) and 2M NaOH (10 ml) for 2 h. This was then cooled to room temperature, aq. HCl was added to adjust the pH to 5, at which point the product precipitated and was filtered off, washed with water, and dried to give the crude product (−350 mg).

Workup

  1. customat which point the product precipitated
  2. filtrationwas filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a702d76843aa4f859b2053f726864fab
Source dataset
uspto-grants-2013_12
Patent number
US08614212B2

Reaction notes

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