1-Butanol → 1-(p-Nitroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
Reaction equation
C(OC(OCC)C[N:6]([C:16](=O)[CH3:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)C.[ClH:22].[OH:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[OH:33])[CH2:27][CH2:28][NH2:29].C(O)CCC>O>[ClH:22].[N+:13]([C:10]1[CH:9]=[CH:8][C:7]([NH:6][CH2:16][CH:17]2[C:30]3[C:26](=[CH:25][C:24]([OH:23])=[C:32]([OH:33])[CH:31]=3)[CH2:27][CH2:28][NH:29]2)=[CH:12][CH:11]=1)([O-:15])=[O:14]Participants
5
Procedure
A mixture of N-acetyl-p-nitroanilinoacetaldehyde diethyl acetal (1 g), 3,4-dihydroxyphenethylamine hydrochloride (1 g), n-butyl alcohol (10 ml) and water (1.5 ml) was refluxed for 7 hours. In the course of the reaction, the above-mentioned acetal (2.5 g) was added to the mixture, twice in 0.5 g portions and five times in 0.3 g portions, one every hour. The reaction mixture was filtered and the filtrate was concentrated to dryness. The residue was pulverized by adding ether and the powder was collected by filtration, washed with ethyl acetate and water and dried to give 1-(p-nitroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1 g), mp 238° to 239° C. (dec).
Workup
- temperaturewas refluxed for 7 hours
- customIn the course of the reaction
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated to dryness
- additionby adding ether
- filtrationthe powder was collected by filtration
- washwashed with ethyl acetate and water
- customdried
Sources & evidence
- ORD record
- ord-a568021fc9c549b7a51d485b9981a60b
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220647
Reaction notes
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