Sodium Chloride → HCID 13187707, compound

HRID 1719516Notes

Reaction equation

[C:1]([C:4]1([NH:18][C:19]([CH3:21])=[O:20])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([O:16]C)[CH:8]=[CH:9][C:10]=2[O:14]C)[CH2:5]1)(=[O:3])[CH3:2].[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>C(O)(=O)C(O)=O>[C:1]([C:4]1([NH:18][C:19]([CH3:21])=[O:20])[CH2:5][C:6]2[C:7]([OH:16])=[C:8]3[C:9]([C:22](=[O:27])[C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[C:25]3=[O:26])=[C:10]([OH:14])[C:11]=2[CH2:12][CH2:13]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

2-Acetyl-2-acetamino-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene (2.8 g), phthalic anhydride (3.4 g), aluminum chloride (40 g) and sodium chloride (8 g) were pulverized and mixed well and charged in a flask previously heated at 180° C. Heating was continued at 180° C. to melt the contents. After melting, heating was further continued for 2 minutes. Then, the temperature was quickly lowered to room temperature, followed by incorporation of a saturated oxalic acid solution (500 ml) cooled with ice water therein. The resultant mixture was stirred at room temperature for 10 minutes. The precipitated crystals were collected by filtration to give 9-acetyl-9-acetamino-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione. M.P., 295°-303° C. (decomp.).

Workup

additionmixed well
additioncharged in a flask
temperatureHeating
customwas continued at 180° C.
temperatureheating
customwas quickly lowered to room temperature
filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-c8b0e4c130544613bc94d442b75be651
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04540695

Reaction notes

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