Potassium Carbonate → 3-(1H-indazol-1-yl)phenol

HRID 1050638Notes

Reaction equation

HRID 1050638 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>Br.O>[N:9]1([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[N:10]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 112530791-(3-Methoxyphenyl)-1H-indazole

Product 1

HCID 644360733-(1H-indazol-1-yl)phenolYield 94%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 1-(3-methoxyphenyl)-1H-indazole 1 (6.50 g, 28.98 mmol) in hydrogen bromide acid (45 mL, 48%) was refluxed (110-120° C.) for 23 hours at an atmosphere of nitrogen. Then the mixture was cooled down to ambient temperature and neutralized with a solution of K2CO3 in water until there was no gas to generate. Then the precipitate was filtered off and washed with water several times. The collected solid was dried in air to afford the product as a brown solid 5.70 g in 94% yield. 1H NMR (DMSO-d6, 400 MHz): δ 6.63 (dd, J=8.4, 2.0 Hz, 1H), 7.00-7.03 (m, 2H), 7.08 (t, J=7.6 Hz, 1H), 7.20 (t, J=7.6 Hz, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 8.17 (s, 1H), 9.67 (bs, 1H). 13C NMR (DMSO-d6, 100 MHz): δ 109.08, 110.54, 112.45, 113.63, 121.48, 121.61, 125.05, 127.42, 130.41, 135.48, 138.02, 140.72, 158.35.

Workup

  1. filtrationThen the precipitate was filtered off
  2. washwashed with water several times
  3. customThe collected solid was dried in air

Sources & evidence

ORD record
ord-6e085e9d39694b3d8e9fe16a4c61ee22
Source dataset
uspto-grants-2016_07
Patent number
US09385329B2

Reaction notes

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