HCID 49857273, compound → HCID 49857274, compound

HRID 641200Notes

Reaction equation

HRID 641200 reaction equation
[N:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15](=[O:17])[CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[C:18]2[C:23]3[S:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:22]=3[C:21]([N+:31]([O-])=O)=[CH:20][CH:19]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CC(O)=O.[Zn]>[NH2:31][C:21]1[C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[S:24][C:23]=2[C:18]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[NH:8][C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:16][C:15]3=[O:17])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 49857273HCID 49857273, compound

Product 1

HCID 49857274HCID 49857274, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

In a round bottom flask, 2-morpholin-4-yl-8-(1-nitro-dibenzothiophen-4-yl)-1H-quinolin-4-one (24)(365 mg; 0.798 mmol) was suspended in AcOH (5 mL). Zinc powder (5223.3 mg; 7.98 mmol) was added to this solution and the reaction was stirred at room temperature overnight. The reaction mixture was filtered through Celite™, washed successively with methanol (4×25 mL) and DCM (4×25 mL). The combined organic layers were evaporated under reduced pressure. The residue was stirred with water (50 mL) and aqueous ammonia (15 mL) was added to the solution. The resultant precipitate was collected by filtration. The residue was dried and did not require further purification. The product was obtained as a yellow solid (291.3 mg). Yield=85.4%. Mass Spec.: (m/z) 428.4 [M+1]+ (Rt=3.83 min).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. washwashed successively with methanol (4×25 mL) and DCM (4×25 mL)
  3. customThe combined organic layers were evaporated under reduced pressure
  4. stirringThe residue was stirred with water (50 mL) and aqueous ammonia (15 mL)
  5. additionwas added to the solution
  6. filtrationThe resultant precipitate was collected by filtration
  7. customThe residue was dried
  8. custompurification

Sources & evidence

ORD record
ord-7a70d13b7a3f454f8f6845bf977fcdef
Source dataset
uspto-grants-2010_04
Patent number
US07696203B2

Reaction notes

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