Trifluoroacetic acid → 4-Bromo-6-methoxyquinolin-3-amine

HRID 2356322Notes

Reaction equation

HRID 2356322 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[Br:18])=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[Br:18])=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68455075(4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 684539074-Bromo-6-methoxyquinolin-3-amineYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Bromo-6-methoxy-quinolin-3-yl)-carbamic acid tert-butyl ester (22.7 g, 0.0643 mole) was dissolved in CH2Cl2 (200 mL) and treated with trifluoroacetic acid (100 mL). After 3.5 hr at RT, the mixture was concentrated and the residue was dissolved in water. The solution was made basic with aqueous sodium carbonate. The precipitate was filtered off, washed with water, and dried at 40° C. in vacuo overnight, to give the title compound (16.46 g, 101%) as a white solid: MS (ES) m/e 254/256 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried at 40° C. in vacuo overnight

Sources & evidence

ORD record
ord-a413c1463ba84637aca218e68c0f9fcf
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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