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

HRID 1595466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595466
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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 224628128-Iodo-5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acidAusbeute 6,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 284Formic AcidLösungsmittel

Versuchsvorschrift

1-Oxo-indan4-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 (760 W) in a CEM Microwave (MDS2000) for one minute (T=140 C, P<50 PSI), allowed to cool for 2 min, then irradiated again for one min (T=140 C, 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 gave 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]+.

Aufarbeitung

  1. customThe vessel was irradiated at full power (760 W) in a CEM Microwave (MDS2000) for one minute (T=140 C, P<50 PSI)
  2. temperatureto cool for 2 min
  3. customirradiated again for one min (T=140 C, P<50 PSI)
  4. filtrationfiltered hot
  5. washThe solid was washed with formic acid
  6. customdried on the frit

Quellen und Nachweise

ORD-Eintrag
ord-666d0afc8e134c34ad60fe9bb9208b70
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288099B1

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