Hydrochloric Acid → 3-Formyl-2-pivaloylaminoquinoline

HRID 1167381Notes

Reaction equation

HRID 1167381 reaction equation
[C:1]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Li]CCCC.[CH:23](N1CCOCC1)=[O:24].Cl>C1COCC1.O>[CH:23]([C:17]1[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 20417N-FormylmorpholineHCID 136426922-PivaloylaminoquinolineHCID 178418339Butyllithium

Product 1

HCID 106348213-Formyl-2-pivaloylaminoquinolineYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-pivaloylaminoquinoline (5.00 g, 21.92 mmol) in THF (75 mL) at −78° C. was added dropwise BuLi (5.48 mL, 10 M in hexane, 54.80 mmol). After 2 hours at −78° C. the dianion was quenched by the addition of N-formylmorpholine (3.79 g, 37.88 mmol). The reaction mixture was allowed to warm to room temperature and poured into 2M aqueous HCl (20 mL). The pH of the aqueous phase was adjusted to 7.0 by addition of 2M HCl and the aqueous phase was diluted with water (100 mL) and extracted with diethyl ether (2×100 mL). The organic phase was dried (MgSO4) and evaporated to dryness in vacuo. The crude product was recrystallized from petrol ether/ethyl acetate to give 2.92 g (52%) of the title compound.

Workup

  1. extractionextracted with diethyl ether (2×100 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated to dryness in vacuo
  4. customThe crude product was recrystallized from petrol ether/ethyl acetate

Sources & evidence

ORD record
ord-fe7e77b8997b43dc81d967d472c74966
Source dataset
uspto-grants-2003_09
Patent number
US06617422B1

Reaction notes

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