2-Phenylethanol → 1-Amino-6-chloro-4-hydroxy-2-(2-phenylethoxy)anthracene-9,10-dione

HRID 1789323Notes

Reaction equation

[C:1]1([CH2:7][CH2:8]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(=O)NCCCCC1.C(=O)([O-])[O-].[K+].[K+].[NH2:24][C:25]1[C:38]2[C:37](=[O:39])[C:36]3[C:31](=[CH:32][C:33]([Cl:40])=[CH:34][CH:35]=3)[C:30](=[O:41])[C:29]=2[C:28]([OH:42])=[CH:27][C:26]=1[O:43]C1C=CC=CC=1>CO>[NH2:24][C:25]1[C:38]2[C:37](=[O:39])[C:36]3[C:31](=[CH:32][C:33]([Cl:40])=[CH:34][CH:35]=3)[C:30](=[O:41])[C:29]=2[C:28]([OH:42])=[CH:27][C:26]=1[O:43][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 48.8 g of β-phenylethanol, 45.2 g of ε-caprolactam, 5.2 g of dry potassium carbonate and 18.3 g of 1-amino-2-phenoxy-4-hydroxy-6-chloroanthraquinone (preparation see Example 467c) is heated at 140° C. until, after about 4 hours, the reaction is complete. The mixture at 70° C. is diluted with 100 ccm of methanol, allowed to cool down, filtered with suction, washed with methanol and hot water and dried at 60° C. 14 g, corresponding to 71% of theory, of 1-amino-2-(2-phenylethoxy)-4-hydroxy-6-chloroanthraquinone are obtained, the colour shade of which on silica gel is a pink tinged with blue between Indicator Numbers 50 and 51 (Colour Index Hue Indication Chart).

Workup

temperatureto cool down
filtrationfiltered with suction
washwashed with methanol and hot water
customdried at 60° C

Sources & evidence

ORD record: ord-0b831d043d2d403abc9af91ccf49b8fe
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689171

Reaction notes

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