Hydrochloric Acid → HCID 10172423, compound

HRID 730264Notes

Reaction equation

HRID 730264 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[C:4]([CH3:13])([CH3:12])[CH2:3]1.[CH3:14][C:15]1([CH3:27])[C:23]2[C:18](=[CH:19][C:20]([N+]([O-])=O)=[CH:21][CH:22]=2)N[CH2:16]1.[H-].[Na+].I[CH3:31].O.O.[Sn](Cl)Cl.Cl.C([O:40][CH2:41][CH3:42])C>CN(C=O)C>[C:15]([C:23]1[CH:18]=[CH:19][C:20](/[CH:31]=[CH:42]/[C:41]([NH:11][C:8]2[CH:9]=[C:10]3[C:5]([C:4]([CH3:13])([CH3:12])[CH2:3][N:2]3[CH3:1])=[CH:6][CH:7]=2)=[O:40])=[CH:21][CH:22]=1)([CH3:27])([CH3:16])[CH3:14]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 61436Stannous chloride dihydrateHCID 219594663,3-Dimethyl-6-nitroindolineHCID 534382971,3,3-Trimethyl-2,3-dihydro-1H-indol-6-amine

Product 1

HCID 10172423HCID 10172423, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1,3,3-Trimethylindoline-6-ylamine. A solution of 3,3-dimethyl-6-nitroindoline, Example 32(a), (0.23 g, 1.2 mmol) in anhydrous DMF (15 mL) was magnetically stirred at 25° C. and treated with sodium hydride (0.14 g, 3.6 mmol, 60% dispersion in mineral oil, Aldrich), followed by iodomethane (0.17, 1.3 mmol, Aldrich). The reaction mixture was stirred at 25° C. for 3 h, then quenched with water (40 mL) and extracted with EtOAc (3×30 mL). The combined extract was concentrated in vacuo to provide a residue [MS (ESI, pos. ion) m/z: 207 (M+1)] which was immediately dissolved in ethyl ether (5 mL), magnetically stirred at 0° C., and treated with tin (II) chloride dihydrate (1.7 g, 7.5 mmol, Aldrich) and cond HCl (0.8 mL). The reaction mixture was stirred at 0° C. for 10 min, allowed to warm to 25° C., then stirred at that temperature overnight. The reaction mixture was washed with 10 N NaOH (20 mL) and extracted with EtOAc (3×50 mL). The combined extracts were concentrated in vacuo and purified by silica gel chromatography to provide the title product. MS (ESI, pos. ion) m/z: 177 (M+1).

Workup

  1. customquenched with water (40 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. extractionThe combined extract
  4. concentrationwas concentrated in vacuo
  5. customto provide a residue [MS (ESI, pos. ion) m/z: 207 (M+1)] which
  6. stirringmagnetically stirred at 0° C.
  7. stirringThe reaction mixture was stirred at 0° C. for 10 min
  8. temperatureto warm to 25° C.
  9. stirringstirred at that temperature overnight
  10. washThe reaction mixture was washed with 10 N NaOH (20 mL)
  11. extractionextracted with EtOAc (3×50 mL)
  12. concentrationThe combined extracts were concentrated in vacuo
  13. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-0ed36d387412439fa5c4c42cf4591e11
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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