Water → 6-Fluoroquinolin-3-amine

HRID 1944553Notes

Reaction equation

HRID 1944553 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([F:18])=[CH:13][CH:12]=2)(C)(C)C.FC(F)(F)C(O)=O.O>ClCCCl>[F:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([NH2:7])=[CH:17]2

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66815651(6-Fluoro-quinolin-3-yl)carbamic acid tert-butyl ester

Product 1

HCID 224587126-Fluoroquinolin-3-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (6-fluoro-quinolin-3-yl)-carbamic acid tert-butyl ester (1.3 g, 4.95 mmol) in 1,2-dichloroethane (15 mL) was treated with trifluoroacetic acid (15 mL) and water (1 mL). The resultant solution was stirred at room temperature for 6 hours. The solvents were evaporated in vacuo, and the residue was triturated in diethyl ether. The solid was purified by flash chromatography using a gradient of 2 N ammonia in methanol (0% to 3%) in dichloromethane as the eluant, to give the product as a colorless solid, 0.47 g (59%). MS: m/z 162.9 (MH+).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was triturated in diethyl ether
  3. customThe solid was purified by flash chromatography

Sources & evidence

ORD record
ord-56aa29d356bd4a91ac3c7fd84b161081
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…