Water → HCID 136078943, compound

HRID 55828Notes

Reaction equation

HRID 55828 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[O:21]C)[CH:6]=[CH:5]2.FC1C2C(=CC=C(O)C=2)N=C(C2C=CC(C(O)=O)=CC=2OC)C=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:21][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:12]=1[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[CH:3]=2)[N:8]=1)[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 56959336HCID 56959336, compoundHCID 569610574-(6-Hydroxyquinolin-2-yl)-3-methoxybenzoic acid

Product 1

HCID 136078943HCID 136078943, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70 mg of 4-(6-hydroxyquinolin-2-yl)-3-methoxybenzoic acid (Compound 48) was suspended in 10 ml DCM and 0.25 ml BBr3 was added. The mixture was stirred at room temperature for 2 days. 20 ml water was added to quench the reaction. DCM was removed by evaporation and the precipitate was filtered and washed with water and dried to obtain 29 mg of 3-hydroxy-4-(6-hydroxyquinolin-2-yl)benzoic acid. 1H NMR (DMSO-d6 300 MHz TMS): δ 10.34 (s, 1H), 8.45 (d, 1H), 8.30 (d, 1H), 8.24 (d, 1H), 7.97 (d, 1H), 7.46 (m, 3H), 7.26 (d, 1H), MS (ESI): m/z=282.30 [M+1]+.

Workup

  1. customto quench
  2. customthe reaction
  3. customDCM was removed by evaporation
  4. filtrationthe precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-23abbfb9931746fbb3e3490c2c0bbeb4
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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