Phosphorus oxychloride → HCID 17954540, compound

HRID 859990Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](O)[CH:6]=[C:5]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1.O=P(Cl)(Cl)[Cl:24]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:24])[CH:6]=[C:5]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178516416HCID 178516416, compound

Product 1

HCID 17954540HCID 17954540, compoundYield 60%

Procedure

Prepared using general procedure 3; 6-Bromo-2-hydroxy-4-(3,4-dichlorophenyl)aminoquinoline (1.94 g, 5.05 mmol) and 30 mL of POCl3 were heated to 120° C. for 4 h. Isolation afforded 1.209 g of material (3.00 mmol, 60%). 1H NMR (300 MHz, DMSO): 9.69(s, 1H), 8.71(s, 1H), 7.91(d, 1H, J=8.88 Hz), 7.78(d, 1H, J=8.88 Hz), 7.69(d, 1H, J=8.88 Hz), 7.68(s, 1H), 7.44(dd, 1H, J=8.68, 2.22 Hz), 6.91(m, 1H).

Workup

customPrepared

Sources & evidence

ORD record: ord-fe8985fde7b14c949ce31b57be419b27
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153865B2

Reaction notes

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