6-Chloro-2,3-dihydro-1h-indole → 4-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride

HRID 1597986Notes

Reaction equation

HRID 1597986 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][CH2:21][NH:22]2)=[CH:18][CH:17]=1>C(O)(C)C>[ClH:1].[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][CH2:21][N:22]2[C:2]2[C:11]3[C:6](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2585676-Chloro-2,3-dihydro-1h-indoleHCID 8306804-Chloro-7-nitroquinazoline

Product 1

HCID 189328314-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-7-nitroquinazoline (11.22 g, 53.5 mmol) was slurried into 35 ml isopropanol, treated with 6-chloroindoline (8.25 g, 53.7 mmol), refluxed for three hours, then cooled slowly to room temperature. Product was filtered and air dried overnight to afford bright yellow powder; 13.18 g (68%): M.P. 230° C. (dec); LC-MS: 327 (MH+), 329 ((M+2)H+); Calc. C16H11ClN4O2.HCl: C,52.91; H,3.3; N,15.43; Cl,19.52; Found: C,52.77; H,3.61; N,14.78; Cl,19.62.

Workup

  1. temperaturerefluxed for three hours
  2. filtrationProduct was filtered
  3. customair dried overnight
  4. customto afford bright yellow powder

Sources & evidence

ORD record
ord-c54a2a7d404d4e6199339cd218ba991f
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…