3,4-Dichloroaniline → HCID 178526426, compound

HRID 2185182Notes

Reaction equation

HRID 2185182 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[C:7]2[OH:13].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[Cl:25])[NH2:21]>CN1CCCC1=O>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][C:9]2[N:8]=[C:7]([OH:13])[C:6]3[C:11](=[C:2]([Br:1])[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=3)[N:10]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 178526425HCID 178526425, compound

Product 1

HCID 178526426HCID 178526426, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 8-bromo-2-chloro-6-nitroquinazolin-4-ol (2.96 g) and 3,4-dichloroaniline (4.72 g) in 1-methyl-2-pyrrolidinone (70 mL) was heated at 140° C. for 3 h. The mixture was cooled to room temperature and poured onto ice/water (600 mL). The precipitate which formed was filtered, washed with water (50 mL), diethyl ether (150 mL) and dried in vacuo to afford the title compound (4.18 g). 1H NMR (300 MHz, DMSO-d6) δ11.62 (s, 1H), 9.64 (s, 1H), 8.72-8.65 (m, 3H), 7.61 (s, 1H), 7.60 (5, 1H); HPLC (Method B): 10.56 min. MS (APCI−): m/z 429, 431.

Workup

  1. additionpoured onto ice/water (600 mL)
  2. customThe precipitate which formed
  3. filtrationwas filtered
  4. washwashed with water (50 mL), diethyl ether (150 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a5b8b677cdad4cc288f7017ba95202a1
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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