Water → HCID 50941760, compound

HRID 2420959Notes

Reaction equation

HRID 2420959 reaction equation
O=[C:2]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[NH:3]1.O=P(Cl)(Cl)[Cl:21].CCN(C(C)C)C(C)C.O>C1(C)C=CC=CC=1>[Cl:21][C:2]1[C:11]2[CH:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 50941659HCID 50941659, compound

Product 1

HCID 50941760HCID 50941760, compoundYield 641.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate (1.0 eq, 1.50 g, 5.79 mmol) was suspended in dry toluene (15 ml). POCl3 (1.2 eq, 0.64 mmol, 6.99 mmol) and DIEA (0.8 eq, 0.81 mmol, 4.65 mmol) were added and the mixture vigorously stirred at 120° C. for 3 hours under nitrogen atmosphere. The mixture was hydrolyzed by addition of ice and water. The compound was extracted with CH2Cl2 (4×). The combined extracts were dried over Na2SO4 and the black solution filtered through a pad of celite. After evaporation of the volatiles in vacuo, the resulting solid was triturated in a mixture of AcOEt and hexanes. Filtration and drying provided methyl 4-chlorothieno[3,2-c]quinoline-7-carboxylate as a yellow fluffy solid (1.14 g, 71% yield). LCMS (ES): 95% pure, m/z 278 [M+1]+, 1H NMR (CDCl3, 400 MHz) δ 4.01 (s, 3H), 7.72 (d, J=4.8, 1H), 7.74 (d, J=5.2, 1H), 8.14 (d, J=8.4, 1H), 8.25 (d, J=8.4, 1H), 8.85 (d, J=1.6, 1H) ppm.

Workup

  1. extractionThe compound was extracted with CH2Cl2 (4×)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationthe black solution filtered through a pad of celite
  4. customAfter evaporation of the volatiles in vacuo
  5. customthe resulting solid was triturated in a mixture of AcOEt and hexanes
  6. filtrationFiltration
  7. customdrying

Sources & evidence

ORD record
ord-49af030db1e641349f694421cf49c7a8
Source dataset
uspto-grants-2011_06
Patent number
US07956064B2

Reaction notes

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