3,4-Dichloroaniline → HCID 178518005, compound

HRID 2185184Notes

Reaction equation

HRID 2185184 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]=[C:7]2[OH:13].[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[Cl:22])[NH2:18]>CN1CCCC1=O>[Cl:14][C:15]1[CH:16]=[C:17]([NH:18][C:9]2[N:8]=[C:7]([OH:13])[C:6]3[C:11](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 178517813HCID 178517813, compound

Product 1

HCID 178518005HCID 178518005, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 8-bromo-2-chloroquinazolin-4-ol (0.37 g) and 3,4-dichloroaniline (0.69 g) in 1-methyl-2-pyrrolidinone (8 mL) was heated at 140° C. for 3 h. The mixture was then cooled to room temperature and poured onto ice/water (100 mL). The precipitate which formed was isolated by filtration, washed sequentially with water and diethyl ether, then was dried in vacuo to afford the title compound (0.46 g). 1H NMR (300 MHz, DMSO-d6): δ11.14 (s, 1H), 9.22 (s, 1H), 8.80 (d, J=2.4 Hz, 1H), 8.04 (d, J=7.8 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.57-7.51 (m, 2H), 7.20-7.18 (m, 1H). HPLC Method B: 9.90 min. MS (APCI+): m/z 386, 388. (APCI−): m/z 384, 386. The starting material 8-Bromo-2-chloroquinazolin-4-ol was prepared as follows:

Workup

  1. additionpoured onto ice/water (100 mL)
  2. customThe precipitate which formed
  3. customwas isolated by filtration
  4. washwashed sequentially with water and diethyl ether
  5. customwas dried in vacuo

Sources & evidence

ORD record
ord-b3cb523ca7b34de2901335c0ae2b6a0c
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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