Acetic Acid → 8-Bromo-2-propylthiazolo[4,5-c]quinolin-4-amine

HRID 2305452Notes

Reaction equation

[CH2:1]([C:4]1[S:5][C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:16])[C:7]=2[N:17]=1)[CH2:2][CH3:3].C(O)(=O)C.[Br:22]Br>O>[Br:22][C:13]1[CH:12]=[CH:11][C:10]2[N:9]=[C:8]([NH2:16])[C:7]3[N:17]=[C:4]([CH2:1][CH2:2][CH3:3])[S:5][C:6]=3[C:15]=2[CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Propylthiazolo[4,5-c]quinolin-4-amine (1.0 g, 0.41 mmol) was combined with acetic acid (15 mL) and heated to 60° C. Bromine (0.10 mL, 1.94 mmol) was added dropwise and the reaction mixture was stirred at 60° C. for 18 hours. The reaction mixture was diluted with water and the resulting precipitate was isolated by filtration to provide 0.25 g of 8-bromo-2-propylthiazolo[4,5-c]quinolin-4-amine as a yellow solid, m.p. 177-180° C. Analysis: Calculated for C13H12BrN3S: %C, 48.46; %H, 3.75; %N, 13.04; Found: %C, 47.98; %H, 3.95; %N, 12.70.

Workup

customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record: ord-cb3e7f5364d940ac9584e10ed9cadc93
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06440992B1

Reaction notes

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