1,4-Diamino-2,3-anthraquinonedicarboximide → N-(6'-hydroxyhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide

HRID 638524Notes

Reaction equation

[NH2:1][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]([NH2:18])=[C:4]2[C:19](=[O:23])[NH:20][C:21](=[O:22])[C:3]=12>COC(O)C>[OH:16][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:20]1[C:21](=[O:22])[C:3]2[C:4](=[C:5]([NH2:18])[C:6]3[C:7](=[O:17])[C:8]4[C:13]([C:14](=[O:16])[C:15]=3[C:2]=2[NH2:1])=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:19]1=[O:23]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 1,4-diaminoanthraquinone-2,3-dicarboximide (15.0 parts) and 6-aminopropanol (28.6 parts) in methoxyethanol (200.0 parts) was heated at 120° C. for 6 hours. The reaction mixture was cooled to room temperature, followed by cooling in ice for several hours. Thereafter the resulting mixture was filtered and washed with methanol (600 parts). The product obtained was dried in vacuo for 8 hours at 45° C. yielding N-(6'-hydroxyhexyl)1,4-diaminoanthraquinone-2,3-dicarboximide (17.1 parts, 83%); m.p.: 210°-211° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
temperatureby cooling in ice for several hours
filtrationThereafter the resulting mixture was filtered
washwashed with methanol (600 parts)
customThe product obtained
customwas dried in vacuo for 8 hours at 45° C.

Sources & evidence

ORD record: ord-e5798be771a94e919d0fa078e6278fe6
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04562135

Reaction notes

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