Hydrochloric Acid → 77280-93-4

HRID 1437149Notes

Reaction equation

HRID 1437149 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][OH:5].[N+:6]([C:9]1[C:22]2[C:13](=[N:14][C:15]3[C:20]([C:21]=2OC2C=CC=CC=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1)([O-:8])=[O:7].Cl>C1(O)C=CC=CC=1.CCOCC>[ClH:1].[N+:6]([C:9]1[C:22]2[C:13](=[N:14][C:15]3[C:20]([C:21]=2[NH:2][CH2:3][CH2:4][OH:5])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 74819Ethanolamine HydrochlorideHCID 131933931-Nitro-9-phenoxyacridine

Product 1

HCID 37150477280-93-4Yield 91%

Reagents, catalysts & solvents 2

HCID 996PhenolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
80 °C

Procedure

This compound is synthesized generally using the methods described in EP 38579. Specifically, 2 g of 2-amino-ethanol hydrochloride is added to 6.4 g of 1-nitro-9-phenoxyacridine dissolved in 20 g of freshly distilled phenol. The mixture is heated for 40 minutes at a temperature of 80° C. and then cooled, diluted with ether. It is then poured into dry ether that was acidified with an ethereal solution of hydrogen chloride. The orange colored precipitate of 1-nitro-9-(2-hydroxyethylamino)-acridine hydrochloride, obtained in this way is filtered and crystallized from dry ethanol. The melting point of the compounds obtained was 170° C., with decomposition. Yield 91%. Elementary analysis for the formula: C15H14N3O3Cl:calculated:56.47%; C, 4.42%; H, 13.17%; N. determined: 56.44%; C, 4.40%; H, 13.03%; N.

Workup

  1. customThis compound is synthesized generally
  2. temperaturecooled

Sources & evidence

ORD record
ord-7a8c47f4951448f7a8aa840df89fd1a9
Source dataset
uspto-grants-2009_11
Patent number
US07622478B2

Reaction notes

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