Phthalaldehydic acid → HCID 18949905, compound

HRID 1492921Notes

Reaction equation

C(Cl)(=O)OCC.[C:7]([C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13])([OH:9])=O.C(N(CC)CC)C.Cl.[Cl:26][CH2:27][CH2:28][NH2:29]>C(Cl)(Cl)Cl>[OH:9][CH:7]1[C:10]2[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:13])[N:29]1[CH2:28][CH2:27][Cl:26]

Participants

Conditions

Temperature: 0 °C

Procedure

9.7 ml (0.101 mole) of ethyl chlorocarbonate were dropwise added to a solution of 15.2 g (0.101 mole) of 2-carboxybenzaldehyde in 500 ml of chloroform and 14.1 ml (0.101 mole) of triethylamine, cooled to 0° C. After 45 minutes, a solution of 11.7 g (0.101 mole) of 2-chloroethylamine hydrochloride in 200 ml of chloroform and 14.1 ml (0.101 mole) of triethylamine was dropwise added thereto. The obtained solution was kept at 0°-5° C. for 5 hours. After warming to room temperature, the mixture was washed with water, 5% sodium bicarbonate, again with water and finally dried over sodium sulfate. 19 g of a crude product were obtained, which was purified on silica gel column eluting with methylene chloride-acetone 10/1 (v/v). 7 g of the title product were obtained; mp=133°-134° C. (methylene chloride).

Workup

waitThe obtained solution was kept at 0°-5° C. for 5 hours
temperatureAfter warming to room temperature
washthe mixture was washed with water, 5% sodium bicarbonate, again with water
dry with materialfinally dried over sodium sulfate
custom19 g of a crude product were obtained
customwhich was purified on silica gel column
washeluting with methylene chloride-acetone 10/1 (v/v)

Sources & evidence

ORD record: ord-d93e7164fbcc465bb3f4bf2a45f6c820
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05376673

Reaction notes

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