Hydrogen Bromide → 4-Amino-2-ethylthiazolo[4,5-c]quinolin-7-ol

HRID 913359Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH3:24])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.Br.[OH-].[Na+]>C(O)(=O)C>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]([CH2:23][CH3:24])[S:22][C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=2[N:16]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a round bottom flask containing 7-benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amine (11.3 g, 33.7 mmol) was added a 45 wt. % solution of hydrogen bromide in acetic acid (40 mL). The resulting solution was heated at 65° C. for 2 hours and then cooled in an ice bath. Aqueous sodium hydroxide (50% w/w solution) was added slowly until pH 7 and a pale yellow/green solid formed. The solid was isolated by filtration and air dried to provide 8.4 g of 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol. MS (APCI) m/z=246.0.

Workup

temperaturecooled in an ice bath
customa pale yellow/green solid formed
customThe solid was isolated by filtration and air
customdried

Sources & evidence

ORD record: ord-53ef13f7b8314f9eac63bc1417a9007a
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026366B2

Reaction notes

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