Hydrochloric Acid → HCID 59441893, compound

HRID 1014324Notes

Reaction equation

HRID 1014324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[N:8]([C:15](=[O:24])[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH2:7][CH2:6]2.O.O.[Sn](Cl)Cl.Cl>C(O)C.CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]([C:15](=[O:24])[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 59441895HCID 59441895, compound

Product 1

HCID 59441893HCID 59441893, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-(methyloxy)-1-[3-(4-morpholinyl)propanoyl]-6-nitro-2,3-dihydro-1H-indole (0.44 g, 1.31 mmols) in absolute ethanol (150 mL) and DMA (20 mL) was added tin(II)chloride dihydrate (1.77 g, 7.84 mmols) and 1M HCl (3.0 mL). After overnight stirring, reaction was quenched with excess saturated Na HCO3 solution, stirred for one hr. and filtered through celite which was rinsed with methanol. After organic solvent removal, the aqueous layer was extracted with dichloromethane (2×200 mL), the organic layers were combined, adsorbed to silica gel and purified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH) to afford 5-(methyloxy)-1-[3-(4-morpholinyl)propanoyl]-2,3-dihydro-1H-indol-6-amine. ESIMS (M+H)+=306.

Workup

  1. customreaction
  2. customwas quenched with excess saturated Na HCO3 solution
  3. stirringstirred for one hr
  4. filtrationand filtered through celite which
  5. washwas rinsed with methanol
  6. customAfter organic solvent removal
  7. extractionthe aqueous layer was extracted with dichloromethane (2×200 mL)
  8. custompurified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH)

Sources & evidence

ORD record
ord-5fb7f76d48914713886a20889f882494
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…