Trifluoroacetic acid → HCID 89544106, compound

HRID 2203463Notes

Reaction equation

HRID 2203463 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][N:14]=[C:13]([NH:16]C(=O)OC(C)(C)C)[C:12]=3[CH:24]=2)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:16][C:13]1[C:12]2[CH:24]=[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[OH:25])[CH:9]=[CH:10][C:11]=2[O:15][N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735790HCID 131735790, compound

Product 1

HCID 89544106HCID 89544106, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (5-(5-chloro-2-hydroxyphenyl)benzo[d]isoxazol-3-yl)carbamate (0.80 g, 2.21 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (3 mL). The reaction mixture was stirred at ambient temperature for 4 h and concentrated in vacuo. The residue was triturated in hexanes/diethyl ether (1:1 v/v, 5 mL) and washed with hexanes (10 mL) and ethyl acetate (5 mL) to afford 2-(3-aminobenzo[d]isoxazol-5-yl)-4-chlorophenol as a colorless solid in 97% yield (0.559 g): 1H NMR (300 MHz, DMSO-d6) δ 9.92 (s, 1H), 7.99 (d, J=1.3 Hz, 1H), 7.71 (dd, J=8.7, 1.7 Hz, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.30 (d, J=2.7 Hz, 1H), 7.22 (dd, J=8.6, 2.7 Hz, 1H), 6.98 (d, J=8.6 Hz, 1H), 6.55 (br s, 2H); MS (ES+) m/z 260.9 (M+1), 262.9 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated in hexanes/diethyl ether (1:1 v/v, 5 mL)
  3. washwashed with hexanes (10 mL) and ethyl acetate (5 mL)

Sources & evidence

ORD record
ord-d801e530699148988206ecdeefd5746c
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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