Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl- synthesis
- Product Name:Isoquinoline,1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-
- CAS Number:16620-96-5
- Molecular formula:C12H17NO2
- Molecular Weight:207.2689
Yield:16620-96-5 100%
Reaction Conditions:
Stage #1: 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloridewith sodium hydroxide in methanol; for 0.333333 h;
Stage #2: formaldehyd in methanol;water; for 0.583333 h;
Stage #3: with sodium tetrahydroborate in methanol;water;
Steps:
2.2D Synthesis of 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (10o)
A mixture of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt 10n (2.0 g, 8.7 mmol) and sodium hydroxide (0.35 g, 8.7 mmol) is stirred in methanol (21 ml) for 20 minutes.
Aqueous formaldehyde (37%) (0. 68 mL, 8.7 mmol) is added drop-wise over 5 minutes.
The reaction is stirred for 30 min before sodium borohydride (0.33 g, 8.7 mmol) is added portion-wise over 5 min.
The reaction is stirred overnight.
Reaction is reduced to dryness and ethyl acetate and water are added.
Organic layers are separated and the aqueous layer is extracted with ethyl acetate (2*).
The combined organic layers are washed with brine and dried over Na2SO4.
The solution is reduced to dryness to give compound 10 (quantitative yield) as a white solid, m/z=208 [M+H]+.
References:
US2019/100534,2019,A1 Location in patent:Paragraph 0373; 0374
38973-42-1
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