Hydrochloric Acid → HCID 66856287, compound

HRID 1191319Notes

Reaction equation

HRID 1191319 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:13](=[O:20])[CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C)([O-])C.[K+].Cl>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:12]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:13](=[O:20])[C:14]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[C:7]2[OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 66849352HCID 66849352, compound

Product 1

HCID 66856287HCID 66856287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-bromo-2-[(4-methoxybenzyl)(thiophen-2-ylacetyl)amino]benzoate (2.7 g, 5.7 mmol) was taken into tetrahydrofuran (0.50 M, 11 mL) and to this solution was added potassium tert-butoxide (1.3 g, 11 mmol) at room temp. The reaction was stirred for an hour. The crude reaction mixture was poured into 1 N HCl aq. (100 mL). The product was extracted with ethyl acetate (3×50 mL). The combined organic extractions were dried over magnesium sulfate, filtered, and concentrated in vacuo to yield 6-bromo-4-hydroxy-1-(4-methoxybenzyl)-3-(thiophen-2-yl)quinolin-2(1H)-one as a brown oil. Used without further purification. LCMS (M+H)=441.6.

Workup

  1. customThe crude reaction mixture
  2. extractionThe product was extracted with ethyl acetate (3×50 mL)
  3. extractionThe combined organic extractions
  4. dry with materialwere dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7b41d883f1c47a7997bb614c5f02936
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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