3-Amino-1-propanol → 3,3'-(Benzo[g]phthalazine-1,4-diyldiazanediyl)di(propan-1-ol)

HRID 373004Notes

Reaction equation

HRID 373004 reaction equation
Cl[C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5](Cl)=[N:4][N:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20][OH:21]>>[OH:21][CH2:20][CH2:19][CH2:18][NH:17][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]([NH:17][CH2:18][CH2:19][CH2:20][OH:21])=[N:4][N:3]=1

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 153142771,4-Dichlorobenzo[g]phthalazine

Product 1

HCID 198114393,3'-(Benzo[g]phthalazine-1,4-diyldiazanediyl)di(propan-1-ol)

Conditions

Temperature
130 °C

Procedure

A mixture of 1,4-dichloro-2,3-diaza-anthracene (4.84 g) and dry 1-amino-3-propanol (48 ml) is heated at 130° C. for 24 hours in an autoclave. After cooling to room temperature and dilution of the reaction mixture with a solution of potassium carbonate (96 g) in water (240 ml) a crystalline solid separates which is filtered and recrystallized from aqueous ethanol to give 6.09 g of 1,4-bis[N-(3-hydroxypropyl)amino]-2,3-diaza-anthracene, m.p. 225°-228° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationdilution of the reaction mixture with a solution of potassium carbonate (96 g) in water (240 ml) a crystalline solid separates which is filtered
  3. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-93e7d5b324d24d40a243fb7aaa6c5438
Source dataset
uspto-grants-1992_11
Patent number
US05162320

Reaction notes

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