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Hydrochloric Acid → (3-Bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-acetic acid

HRID 61807
Notes
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Reaction equation

HRID 61807 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:26]=[CH:25][C:9]2[C:10]([CH3:24])([CH3:23])[C:11]3[NH:12][C:13]4[C:18]([C:19]=3[C:20](=[O:21])[C:8]=2[CH:7]=1)=[CH:17][CH:16]=[C:15]([Br:22])[CH:14]=4.COC(=O)CO.[OH-].[Na+].Cl>CO>[Br:22][C:15]1[CH:14]=[C:13]2[C:18]([C:19]3[C:20](=[O:21])[C:8]4[CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:27])=[O:2])[CH:26]=[CH:25][C:9]=4[C:10]([CH3:24])([CH3:23])[C:11]=3[NH:12]2)=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66774Methyl GlycolateHCID 66833939(3-bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-acetic acid methyl ester

Product 1

HCID 66834695(3-Bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-acetic acidYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under the same conditions as the method for synthesizing Compound A7-1, (3-bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-acetic acid methyl ester was prepared from Compound JJ2 and hydroxy-acetic acid methyl ester. The resultant was dissolved in MeOH (0.35 ml), added with aqueous solution of sodium hydroxide (6 mol/1), and stirred at room temperature for 10 min. The reaction solution was added with hydrochloric acid (3 mol/1), extracted with diethyl ether and dried over anhydrous magnesium sulfate. After the concentration under reduced pressure, white solid was obtained, which was then washed with methylene chloride to obtain the title compound (11.2 mg, 48%).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationAfter the concentration under reduced pressure
  4. customwhite solid was obtained
  5. washwhich was then washed with methylene chloride

Sources & evidence

ORD record
ord-bbe0e4ef51854def959a91d02be34b07
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440922B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes