4-Iodophenylhydrazine hydrochloride → 8-Iodo-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid

HRID 1936831노트

반응식

HRID 1936831 반응식
O=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=[O:12])[C:5]=2[CH2:4][CH2:3]1.Cl.[I:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]N)=[CH:18][CH:17]=1>C(O)=O.Cl>[I:15][C:16]1[CH:21]=[CH:20][C:19]2[NH:22][C:2]3[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=[O:12])[C:5]=4[CH2:4][C:3]=3[C:18]=2[CH:17]=1

참가 물질

5

반응물 2

HCID 122087954-Iodophenylhydrazine hydrochlorideHCID 125422061-Oxo-indan-4-carboxylic acid

생성물 1

HCID 224628128-Iodo-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acid

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 284Formic Acid용매

실험 절차

1-Oxo-indan-4-carboxylic acid (0.528 g, 2.99 mmol) and 4-iodophenylhydrazine hydrochloride (0.698 g, 2.58 mmol) were mixed together in a Teflon PFA vessel to form a paste in formic acid (2 mL, 96%) containing 3 drops of concentrated HCl. The vessel was irradiated at full power (760W) in a CEM Microwave (MDS2000) for one minute (T=140C, P<50 PSI), allowed to cool for 2 min, then irradiated again for one min (T=140C, P<50 PSI). The mixture was vacuum filtered hot. The solid was washed with formic acid, and dried on the frit. Chromatography (acetone/hexane) and trituration with diethyl ether have the title compound (0.059 g, 5%) as an tan solid: mp 251° C.; 1H NMR (DMSO-d6): δ 3.98 (s, 2H), 7.30-7.37 (m, 2H), 7.49 (t, 1H), 7.77-7.80 (m, 2H), 7.98 (d, 1H), 11.82 (s, 1H), 13.53 (s, 1H); MS [EI, m/z]: 375 [M]+.

후처리

  1. temperatureto cool for 2 min
  2. filtrationfiltered hot
  3. washThe solid was washed with formic acid
  4. customdried on the frit

출처 및 근거

ORD 기록
ord-aec76d8e2ebf4bf487acebcb571391d7
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391902B1

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