Formic Acid → HCID 23322136, compound

HRID 280274Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[BrH:11].[CH2:12]([N:15]([CH2:28][CH2:29][CH3:30])[CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([OH:27])[C:22]=2[NH2:26])[CH2:17]1)[CH2:13][CH3:14]>C(OCC)C>[BrH:11].[CH2:28]([N:15]([CH2:12][CH2:13][CH3:14])[CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([OH:27])[C:22]=2[NH:26][CH:1]=[O:3])[CH2:17]1)[CH2:29][CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

0.42 ml of acetic anhydride is added all at once to 2 ml of 98% formic acid, kept at 0° C., and the mixture is left at 0° C. for 15 minutes. Then, still using an ice-bath, 1.34 g of 2-dipropylamino-5-amino-6-hydroxy-1,2,3,4-tetrahydronaphthalene hydrobromide are introduced therein with a spatula and the whole is stirred for one hour at 0° C. After 50 ml of diethyl ether have been added and the solid has been filtered off, the latter is recrystallised from a 50/50 methanol/ethyl acetate mixture. This gives 1 g of the final product melting at 213° C. (with decomposition).

Workup

customkept at 0° C.
filtrationthe solid has been filtered off
customthe latter is recrystallised from a 50/50 methanol/ethyl acetate mixture

Sources & evidence

ORD record: ord-d0d94c73bc484afeaf2724708fe7c42d
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588747

Reaction notes

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