Methanol → HCID 20066103, compound

HRID 359129Notes

Reaction equation

HRID 359129 reaction equation
[OH:1][CH2:2][C:3]([CH3:23])([CH3:22])[CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[Br:24]Br.CO.O>N1C=CC=CC=1>[Br:24][C:9]1[C:10]2[C:11](=[O:21])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:20])[C:19]=2[C:6]([NH:5][CH2:4][C:3]([CH3:23])([CH3:22])[CH2:2][OH:1])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24408BromineHCID 20066104HCID 20066104, compound

Product 1

HCID 20066103HCID 20066103, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
92.5 °C

Procedure

To a solution of 1-[(3-hydroxy-2,2-dimethylpropyl)amino]anthraquinone (88.0 g, 0.28 mol) in pyridine (400 mL) is added bromine (48.0 g, 0.30 mol) with vigorous agitation, allowing the temperature to rise to about 40° C. The reaction is completed by heating at 90 to 95° C. for 6 hours and then allowed to cool. Methanol (200 mL) is added, stirring continued for about 2 hours at room temperature and the product is then drowned into water with thorough stirring. The solids are collected by filtration, washed with water and dried in air to give 101.3 g of 4-bromo-l-[(3-hydroxy-2,2-dimethyl-propyl) amino]anthraquinone. The identity of the product is confirmed by mass spectrometry analysis.

Workup

  1. customto rise to about 40° C
  2. temperatureto cool
  3. filtrationThe solids are collected by filtration
  4. washwashed with water
  5. customdried in air

Sources & evidence

ORD record
ord-b287fbbdeacc40f3868f1c9e520f614d
Source dataset
uspto-grants-1991_03
Patent number
US04999418

Reaction notes

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