Hydrochloric Acid → HCID 59441918, compound

HRID 1014320Notes

Reaction equation

HRID 1014320 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:23])[CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]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:23])[CH2:16][N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 59441669HCID 59441669, compound

Product 1

HCID 59441918HCID 59441918, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-(methyloxy)-1-(4-morpholinylacetyl)-6-nitro-2,3-dihydro-1H-indole (0.56 g, 1.74 mmol) in absolute ethanol (100 mL) and DMA (20 mL) was added tin(II)chloride dihydrate (2.36 g, 10.45 mmol) and 1M HCl (1.0 mL). After overnight stirring, reaction was quenched with excess saturated NaHCO3 solution, stirred for one hr, filtered through celite which was and rinsed with methanol. After organic solvent removal, the aqueous layers were extracted with dichloromethane (2×200 mL), the combined organic layers were adsorbed to silica gel and purified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH) to afford 5-(methyloxy)-1-(4-morpholinylacetyl)-2,3-dihydro-1H-indol-6-amine. ESIMS (M+H)+=292.

Workup

  1. customreaction
  2. customwas quenched with excess saturated NaHCO3 solution
  3. stirringstirred for one hr
  4. filtrationfiltered through celite which
  5. washrinsed with methanol
  6. customAfter organic solvent removal
  7. extractionthe aqueous layers were extracted with dichloromethane (2×200 mL)
  8. custompurified by column chromatography (DCM to 5% MeOH/DCM+0.1% NH4OH)

Sources & evidence

ORD record
ord-a9540e60aeb349c899a2c700dff13902
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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