Ammonium Chloride → 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reaction equation

Br.O[CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[Cl:14].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[NH4+]>>[ClH:13].[Cl:13][C:9]1[C:8]([Cl:14])=[C:7]2[C:12]([CH2:3][CH2:4][NH:5][CH2:6]2)=[CH:11][CH:10]=1

Participants

Reactant 3

HCID 25517Ammonium Chloride

HCID 6451240Aluminum(III) Chloride

HCID 70568099HCID 70568099, compound

Product 1

HCID 1239197,8-Dichloro-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 150.2%

Procedure

Using the same reaction conditions and methods of isolation N-hydroxyethyl-2,3-dichlorobenzylamine hydrobromide (2.0 g, 6.0 mm) was reacted in a melt of 5 g (37.5 mm) of aluminum chloride-0.3 g (5.6 mm) of ammonium chloride to give 1.19 g (75.3%) of 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride which was 95.1% pure by high pressure liquid chromatography.

Sources & evidence

ORD record: ord-707323780f484bc786781b6b1459fdcb
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04251660

Reaction notes

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