Water → HCID 58082858, compound

HRID 403257Notes

Reaction equation

HRID 403257 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([OH:11])[CH2:7][CH2:8][C:9]=2[CH:10]=1.C(N(CC)CC)C.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=[O:11])[CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 580828163-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

Product 1

HCID 58082858HCID 58082858, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-ol (570 mg, 3.36 mmol) in dimethylsulphoxide (17.7 ml) was treated at room temperature with triethylamine (2.81 ml, 20.2 mmol) followed by sulfur trioxide-pyridine complex (1.6 g, 10.1 mmol). The solution was stirred at room temperature for 1 hour. After completion, the reaction mixture was treated with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, then evaporated leaving a dark red liquid. The crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=70:30 to 30:70 as the eluent. The 3-chloro-5,6-dihydro-[1]pyrindin-7-one was obtained as a pink solid (472 mg, 84%); (calculated) C8H6ClNO [167.60]; (found) [M+H]+=168.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customevaporated
  4. customleaving a dark red liquid
  5. customThe crude material was purified by flash chromatography on silica gel using a gradient of heptane/ethyl acetate=70:30 to 30:70 as the eluent

Sources & evidence

ORD record
ord-9b3c2401318d423ea00a9503aaf88eb0
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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