Hydrochloric Acid → HCID 71238374, compound

HRID 1846651Notes

Reaction equation

HRID 1846651 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([Br:21])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)C.O.[OH-].[Na+].Cl>CO>[Br:21][C:15]1[CH:16]=[C:17]([N+:18]([O-:20])=[O:19])[C:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4]([OH:22])=[O:3])[CH2:11][CH2:10]2)=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 71238334HCID 71238334, compound

Product 1

HCID 71238374HCID 71238374, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 1.00 g (2.69 mmol) of (5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in a 1:1 mixture of water:methanol (50 mL) is added 2.0 mL (5.0 mmol) of sodium hydroxide as a 10% aqueous solution. The mixture is heated at 60° C. for 1 hour then cooled to room temperature and the pH of the mixture is adjusted to approximately pH 5 by the addition of a 2 N solution of hydrochloric acid. The mixture is extracted with ethyl acetate and the combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 0.700 g (75.7%) of (5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid as an orange oil. No further purification is performed.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe combined organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d15c0129a744d0d802dcb86bb28720e
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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