Hydrochloric Acid → 4-(Anilinomethylidene)-1-benzoxepine-3,5(2H,4H)-dione

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Reaction Steps

A quantity of 10.0g (0.049 mole) of 2,3-dihydro-5-hydroxy-3-oxo-1-benzoxepin-4-carboxaldehyde was added to 15g of aniline. The temperature rose to 45° as most solid went into solution. The dark mixture was heated at 105°-110° for 10 minutes and cooled. Ether (500ml) and 300ml of cold 2N hydrochloric acid were added, and the mixture was stirred for 5 minutes. The entire mixture was filtered to remove the dark, suspended insolubles. The ether phase of the filtrate was washed well with water, dried (Na2SO4) and concentrated to give 8.0g (58%) of crude product; m.p. 94°-96°. Recrystallization from ethyl acetate gave pure, orange-tan crystals; m.p. 98°-100°.

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