Hydrochloric Acid → HCID 59410166, compound

HRID 2405016Notes

Reaction equation

HRID 2405016 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20](O)=[O:21])[C:14]1=[O:23].Cl>O1CCCC1.C(OCC)(=O)C>[OH:21][CH2:20][CH2:19][C:15]1[C:14](=[O:23])[N:13]([C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[CH2:3][O:2][CH3:1])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68209669{1-[2-(Methoxymethyl)-4-nitrophenyl]-2-oxo-1,2-dihydropyridin-3-yl}acetic acid

Product 1

HCID 59410166HCID 59410166, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 37.7 g (109 mmol) of {1-[2-(methoxymethyl)-4-nitrophenyl]-2-oxo-1,2-dihydropyridin-3-yl}acetic acid in 310 ml of tetrahydrofuran were introduced as initial charge at RT, and 53.3 g (327 mmol) of borane-diethylaniline complex were added, at first carefully then, after the considerable foaming has abated, rapidly. The reaction mixture was stirred overnight at RT, diluted with 500 ml of ethyl acetate and admixed with 1N hydrochloric acid (1.55 l), at first carefully (considerable foam formation), then rapidly. The reaction mixture was after-stirred for 30 min, the organic phase was separated off and the aqueous phase was extracted again with 500 ml of ethyl acetate. The combined organic phases were washed twice with in each case 500 ml of 1N hydrochloric acid, washed once with 200 ml of 1N sodium hydroxide solution, dried over sodium sulphate, filtered and evaporated to dryness on a rotary evaporator. The residue was chromatographically purified firstly over 500 g of silica gel (0.04-0.06 mm) with methanol:dichloromethane 5:95 then 1:9 and again over 500 g of silica gel (0.04-0.06 mm) with acetone:dichloromethane 3:7. 14.2 g (43%) of the desired product were obtained here.

Workup

  1. additionas initial charge at RT
  2. addition53.3 g (327 mmol) of borane-diethylaniline complex were added
  3. stirringThe reaction mixture was after-stirred for 30 min
  4. customthe organic phase was separated off
  5. extractionthe aqueous phase was extracted again with 500 ml of ethyl acetate
  6. washThe combined organic phases were washed twice with in each case 500 ml of 1N hydrochloric acid
  7. washwashed once with 200 ml of 1N sodium hydroxide solution
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness on a rotary evaporator
  11. customThe residue was chromatographically purified firstly over 500 g of silica gel (0.04-0.06 mm) with methanol:dichloromethane 5:95

Sources & evidence

ORD record
ord-2b8346f5d6ef4a83bd323cc01b1eb8ad
Source dataset
uspto-grants-2014_08
Patent number
US08802860B2

Reaction notes

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