Phosphorus oxychloride → HCID 17954567, compound

HRID 859988Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](O)[CH:8]=[C:7]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]>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:24])[CH:8]=[C:7]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 178516419HCID 178516419, compound

Product 1

HCID 17954567HCID 17954567, compoundYield 20%

Procedure

Prepared using general procedure 3; 8-Fluoro-2-hydroxy-4-(3,4-dichlorophenyl)aminoquinoline (3.2 g, 9.90 mmol) and 23 mL of POCl3 were heated to 120° C. for 4 h. Isolation afforded 0.69 g of material (1.98 mmol, 20%). 1H NMR (300 MHz, DMSO): 9.50(s, 1H), 8.17(d, ?H, J=7.67 Hz), 8.04(d, 1H, J=5.25 Hz), 7.79(d, 1H, J=5.65 Hz), 7.71(d, 1H, J=8.88 Hz), 7.61(m, 1H), 7.45(dd, 1H, J=8.88, 2.42 Hz), 6.88(s, 1H).

Workup

customPrepared

Sources & evidence

ORD record: ord-92d7605630fe4a118836308250ecf058
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153865B2

Reaction notes

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