Dichloromethane → 2-Chloroquinolin-6-ol

HRID 1627680Notes

Reaction equation

HRID 1627680 reaction equation
N1C(C2C=CC([C:12]3[C:21](C)=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:23]C)[CH:18]=4)[N:13]=3)=CC=2)=NN=N1.B(Br)(Br)Br.C(Cl)[Cl:30]>>[Cl:30][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:23])[CH:18]=2)[N:13]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 178487824HCID 178487824, compound2×

Product 1

HCID 221325772-Chloroquinolin-6-olYield 70%

Conditions

Temperature
25 °C

Procedure

To a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBr3 (6 mL, 62.2 mmol) dropwise at 0° C. The reaction mixture was stirred at 25° C. for 2 hours, then quenched with aqueous saturated NH4Cl (50 mL) and filtered. The filtrate was extracted with CH2Cl2/MeOH (v/v=10/1, mL×2) and the combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-chloroquinolin-6-ol (1.30 g, yield 70%) as yellow solid. 1H NMR (CDCl3 300 MHz): δ 7.95 (t, J=8.1 Hz, 2H), 7.35 (dd, J=6.0, 3.3 Hz, 2H), 7.13 (d, J=2.7 Hz, 1H).

Workup

  1. customquenched with aqueous saturated NH4Cl (50 mL)
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with CH2Cl2/MeOH (v/v=10/1, mL×2) and the combined organic layers
  4. washwere washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cb5edafccb64230984e248dea198e1f
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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