3,4-Dichloroaniline → HCID 178516418, compound

HRID 859983Notes

Reaction equation

HRID 859983 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][C:2]=1[OH:12].[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[Cl:21])[NH2:17]>CN1C(=O)CCC1>[Cl:13][C:14]1[CH:15]=[C:16]([NH:17][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[C:2]([OH:12])[CH:3]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 178516418HCID 178516418, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,4-quinolinediol (10.0 g, 62.1 mmol) and 3,4-dichloroaniline (13.1 g, 80.7 mmol) were heated to 190° C. in 25 mL NMP for 48 h. After heating was discontinued, solids began to precipitate. These were collected, treated with 8.5 mL of HCl in isopropanol and sonicated in a 4:1 mixture of acetone:isopropanol. After 2.5 h of sonication, the solids were collected. The sonication cycle was repeated to afford 6.79 g of material (19.9 mmol, 32%). 1H NMR (300 MHz, DMSO): 12.7 (s,1 H), 9.34 (s, 1 H), 8.41 (d, 1 H, J=9 Hz), 7.71 (m, 3 H), 7.6 (d, 1 H, J=8.1 Hz), 7.44 (m, 2 H), 6.25 (s, 1 H), 6.08 (broad s, 1 H).

Workup

  1. temperatureAfter heating
  2. customto precipitate
  3. customThese were collected
  4. additiontreated with 8.5 mL of HCl in isopropanol
  5. customsonicated in a 4:1 mixture of acetone
  6. customAfter 2.5 h of sonication
  7. customthe solids were collected
  8. customThe sonication cycle

Sources & evidence

ORD record
ord-5c99ba7e09bb49b4abb9cefc9474b627
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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