Hydrochloric Acid → HCID 68701440, compound

HRID 42642Notes

Reaction equation

HRID 42642 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=3)[CH:14]=2)[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[C:8]=1[OH:9].[Cl-].[Al+3].[Cl-].[Cl-].N1C=CC=CC=1.Cl>ClCCCl>[N+:10]([C:7]1[C:8]([OH:9])=[C:3]([OH:2])[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[N:20]=3)[CH:14]=2)[CH:6]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6451240Aluminum(III) ChlorideHCID 68700541HCID 68700541, compound

Product 1

HCID 68701440HCID 68701440, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-methoxy-5-nitro-3′-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-4-ol (0.288 g, 0.738 mmol) in 1,2-dichloroethane (10 mL) cooled in an ice-water bath was added aluminium chloride (0.123 g, 0.922 mmol) in one portion followed by pyridine 0.233 g, 2.95 mmol) dropwise. The resulting red suspension was stirred at 80° C. for two hours, then cooled to room temperature and poured onto cold 2 N aqueous hydrochloric acid (100 mL). The precipitate was filtered off, washed with water and dried to give 5-nitro-3′-(6-(trifluoromethyl)pyridin-2-yl)biphenyl-3,4-diol, 0.164 g, (59%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-badfea930b6a45b793feba79f82ae152
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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