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3-Methoxypropylamine → Quinizarin

HRID 34898
Notes
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Reaction equation

HRID 34898 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1.B(O)(O)O.[CH3:23][O:24][CH2:25][CH2:26][CH2:27][NH2:28]>O>[CH3:23][O:24][CH2:25][CH2:26][CH2:27][NH:28][C:4]1[CH:3]=[C:2]([OH:1])[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]=1[OH:18].[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 16723-MethoxypropylamineHCID 6688QuinizarinHCID 7628Boric Acid

Product 2

HCID 6688QuinizarinHCID 884361,4-Dihydroxy-2-((3-methoxypropyl)amino)anthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

2-(methoxypropylamino)-1,4-dihydroxyanthraquinone was prepared as follows: 60 grams of 1,4-dihydroxyanthraquinone, 15.5 grams of boric acid, and 89 grams of methoxypropylamine were slurried in 125 ml of water. The slurry was stirred and heated to 65° Celsius, and a strong stream of air was bubbled through it. These conditions were maintained about nine hours, or until thin layer chromatography of the reaction mixture failed to isolate any, 1,4-dihydroxyanthraquinone.

Workup

  1. customa strong stream of air was bubbled through it
  2. temperatureThese conditions were maintained about nine hours

Sources & evidence

ORD record
ord-bdd196d979a84c5da73851f747171d88
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764474

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes