Triphenylphosphine → 3-Chloromethyl-2-iodoquinoline

HRID 258118

반응식

HRID 258118 반응식
O[CH2:2][C:3]1[C:4]([I:13])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:33]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:33][CH2:2][C:3]1[C:4]([I:13])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 13527196(2-Iodoquinolin-3-yl)methanol

생성물 1

HCID 110987133-Chloromethyl-2-iodoquinoline수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
-23 °C

실험 절차

To a stirred mixture of 3-hydroxymethyl-2-iodoquinoline prepared in accordance with Example 10 above (350 mg, 1.23 mmol) and triphenylphosphine (483 mg, 1.84 mmol) in 10 mL of dry DMF at -23° C. was added N-chlorosuccinimide (246 mg, 1.84 mmol), and the mixture was stirred for 1 h at -23° C. After the addition of 40 mL of dilute aqueous NaHCO3, the mixture was extracted with ethyl acetate (20 mL) and then ether (2×15 mL). The combined organic extracts were washed successively with 20-mL portions of dilute NaHCO3, water and brine, and were dried over MgSO4. Concentration and purification of the residue by radial PLC (silica gel, 10% ethyl acetate/hexanes) afforded 312 mg (84%) of 3-chloromethyl- 2-iodoquinoline as a white crystalline solid: mp 138°-140° C. Recrystallization from hexanes afforded an analytical sample as colorless needles: mp 139°-140° C. 1H NMR (300 MHz, CDCl3) δ 8.17 (s, 1H), 8.07 (d, 1H, J=9 Hz), 7.84 (d, 1H, J=9 Hz), 7.75 (t, 1H, J=9 Hz), 7.62 (t, 1H, J=9 Hz), 4.80 (s, 1H); IR (nujol) 1585, 1555, 1260, 1010, 780, 755, 710 cm-1.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (20 mL)
  2. washThe combined organic extracts were washed successively with 20-mL portions of dilute NaHCO3, water and brine
  3. dry with materialwere dried over MgSO4
  4. concentrationConcentration and purification of the residue by radial PLC (silica gel, 10% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-b0065abafb9f4bc7885a73ef7ee6be93
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264579

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