Phosphorus oxychloride → HCID 17954548, compound

HRID 859991Notes

Reaction equation

HRID 859991 reaction equation
[F: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]>>[F: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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516420HCID 178516420, compound

Product 1

HCID 17954548HCID 17954548, compoundYield 29%

Procedure

Prepared using general procedure 3; 6-Fluoro-2-hydroxy-4-(3,4-dichlorophenyl)aminoquinoline (2.136 g, 6.6 mmol) and 30 mL of POCl3 were heated to 120° C. for 4 h. Isolation afforded 0.654 g of material (1.914 mmol, 29%). 1H NMR (300 MHz, DMSO): 9.55(s, 1H), 8.27(dd, 1H, J=10.50, 2.02 Hz), 7.92(dd, 1H, J=8.88, 5.65 Hz), 7.70(m, 3H), 7.45(dd, 1H, J=8.48, 2.02 Hz), 6.90(s, 1H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b6031970149140be919066efeb90374b
Source dataset
uspto-grants-2006_12
Patent number
US07153865B2

Reaction notes

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