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Dimethylformamide → N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

HRID 506974
Notes
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Reaction equation

HRID 506974 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=O)[C:9]2=[O:12])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.CN(C=O)C.[CH2:32]([NH2:34])[CH3:33]>C(Cl)Cl.C1COCC1.[OH-].[Na+]>[CH2:32]([NH:34][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:13]([N:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=3)[C:9]2=[O:12])[CH:14]=1)[CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6341EthylamineHCID 24386Thionyl ChlorideHCID 670185873-(7-hydroxy-1-oxo-1H-isoquinolin-2-yl)-4-methylbenzoic acid

Product 1

HCID 11674186N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

Reagents, catalysts & solvents 3

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (140 mg) in methylene chloride (3 ml) was added thionyl chloride (40 μl) and DMF (40 μl) and the solution heated to 40° C. for 35 minutes. The reaction mixture was cooled to room temperature and 2M ethylamine in THF (2.1 mL) was added and the reaction stirred at room temperature for 2 hours. The reaction was dissolved in 1N NaOH and washed with ethyl acetate. The aqueous layer was acidified to pH 3 and extracted with ethyl acetate (×3). The organic layers were dried (magnesium sulfate) and concentrated to yield N-ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a solid (88 mg); NMR Spectrum: (DMSOd6) 1.11 (t, 3H), 2.09 (s, 3H), 3.30 (m, 2H), 6.66 (d, 1H), 7.11 (d, 1H), 7.25 (d, 1H), 7.49 (d, 1H), 7.60 (s, 1H), 7.61 (d, 1H), 7.77 (s, 1H), 7.89 (d, 1H), 8.47 (s, 1H); Mass Spectrum: M+H+ 323.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate (×3)
  4. dry with materialThe organic layers were dried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1fdd5ec915254d9cac1183d3cb429774
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786115B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes