Acetic Acid → HCID 68587091, compound

HRID 17533Notes

Reaction equation

HRID 17533 reaction equation
[CH3:1][N:2]([CH3:25])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:11]([C:20]#[N:21])=[C:10]([N+:22]([O-])=O)[CH:9]=2)[CH2:4]1.C(O)(=O)C.O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl.C(OCC)(=O)C.CO>[NH2:22][C:10]1[CH:9]=[C:8]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:1])[CH3:25])[CH2:4]2)[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]=1[C:20]#[N:21]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 68586542HCID 68586542, compound

Product 1

HCID 68587091HCID 68587091, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

6-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-4-nitrobiphenyl-3-carbonitrile (I-242) (7.9 g, 23.5 mmol) was dissolved in concentrated hydrochloric acid (40 ml), and at room temperature, acetic acid (4.0 ml, 70.5 mmol) and methanol (10 ml) were added, followed by cooling at 0° C., and tin(II) chloride dihydrate (15.9 g, 70.5 mmol) was gradually added. After stirred at the same temperature for 20 minutes, this was further stirred at room temperature for 20 minutes. At room temperature, methanol (30 ml) was added to the suspension, followed by stirring at the same temperature for 24 hours. The reaction liquid was fractionated with ethyl acetate and aqueous 1 M sodium hydroxide solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was subjected to column chromatography with silica gel, and the fraction with chloroform:methanol=95:5 gave the entitled compound (6.475 g, 90%) as a pale brown gel.

Workup

  1. stirringthis was further stirred at room temperature for 20 minutes
  2. stirringby stirring at the same temperature for 24 hours
  3. customThe reaction liquid
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-a40ef0f6b3394eb8975030275c29634e
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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