Triethylamine → HCID 22181628, compound

HRID 2217468Notes

Reaction equation

HRID 2217468 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17].C(N(CC)CC)C.CC(C)([O-])C.[K+]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.C1COCC1.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:1]2[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2=[O:17])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 778882-Amino-5-nitropyridineHCID 5211735-Bromovaleryl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22181628HCID 22181628, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

See Example 75a. 2-Amino-5-nitro-pyridine (2.0 g, 14.3 mmol), 5-bromo-pentanoyl chloride (2.86 g, 14.3 mmol), triethylamine (2.39 g, 17.2 mmol), catalytic DMAP were heated at reflux in toluene (70 mL) 22 h. The reaction was allowed to cool to RT, concentrated and the resulting oil portioned between EtOAc and water. The organic layer was separated, washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate produced an oil which was dissolved in THF (140 mL). Potassium tert-Butoxide (1.68 g, 15.0 mmol) was added portion-wise and the reaction stirred at RT for 2h. Water was then added, and the reaction extracted with EtOAc. The organics were then washed with brine and dried over MgSO4. Purification of the crude material by mplc revealed the product as an orange solid. MS: APCI (AP+): 222.1 (M)+.

Workup

  1. concentrationconcentrated
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customConcentration of the filtrate produced an oil which
  7. extractionthe reaction extracted with EtOAc
  8. washThe organics were then washed with brine
  9. dry with materialdried over MgSO4
  10. customPurification of the crude material by mplc

Sources & evidence

ORD record
ord-ef80885d9ef14aa1a167f55242bc8dc6
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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