HCID 22229231, compound → HCID 18693204, compound

HRID 1870733Notes

Reaction equation

HRID 1870733 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12]C)[CH:7]=1)=[O:5]>Br>[NH2:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)=[O:5]

Participants

3

Reactant 1

HCID 22229231HCID 22229231, compound

Product 1

HCID 18693204HCID 18693204, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-Amino-4-chloro-3'-methoxybenzophenone (3.75 g, 14.3 mmol) was dissolved in 90 mL of 48% hydrobromic acid and the solution was heated at refluxed for 12 h. The solvent was removed by rotary evaporation and the resulting red solid was distributed between saturated sodium bicarbonate (200 mL) and CH2Cl2 (250 mL). The aqueous layer was washed with CH2Cl2 (2×100 mL) and the combined organic layers were dried with sodium sulfate, filtered through celite and concentrated in vacuo to afford 2.95 g (83% yield) of 2-amino-4-chloro-3'-hydroxybenzophenone (22b) as a yellow solid: mp 137-138° C., Rf 0.15 (75:25, hexanes/ethyl acetate). 1H NMR (500 MHz, CDCl3); δ 6.16 (b, 2), 6.55 (dd, 1, J=2.0, 8.5), 6.72 (d, 1, J=1.9), 6.99 (dd, 1, J=2.5, 8.1), 7.05 (t, J=2.0), 7.12 (d, 1, J=7.8), 7.30 (t, 1, 7.8), 7.38 (d, 1, J=8.6). 13C NMR (101 MHz): δ 115.6, 116.1, 116.2, 118.4, 120.3, 121.6, 126.1, 129.5, 135.9, 142.2, 154.3. HRMS (FAB, m-nitrobenzyl alcohol) calcd for C13H10CINO2 (M+H) 248.0046, found 248.0484.

Workup

  1. temperaturethe solution was heated
  2. temperatureat refluxed for 12 h
  3. customThe solvent was removed by rotary evaporation
  4. washThe aqueous layer was washed with CH2Cl2 (2×100 mL)
  5. dry with materialthe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered through celite and
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92f1775262c742db8129841ea84fd9ea
Source dataset
uspto-grants-2000_08
Patent number
US06100254

Reaction notes

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