Benzene, 1-(chloromethyl)-2-fluoro- → 1,2,3,4-Tetrahydroisoquinolin-4-ol

HRID 648088Notes

Reaction equation

HRID 648088 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2(CC3C=CC=CC=3[O:11]2)[CH2:3][NH:2]1.[H][H].FC1C=CC=CC=1CCl.FC1C=CC=CC=1CBr>>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[CH2:3][NH:2]1

Participants

5

Reactant 4

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 67968alpha-Bromo-o-fluorotolueneHCID 15917444spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]HCID 178418361HCID 178418361, compound

Product 1

HCID 117447921,2,3,4-Tetrahydroisoquinolin-4-ol

Procedure

To prepare the parent ring system 7, i.e., the spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] 1 wherein R is hydrogen, a 2,3-dihydro-4(1H)isoquinoline 3 wherein R is loweralkyl or benzyl is treated with a Grignard reagent 4, prepared from a 2-fluorobenzyl chloride or 2-fluorobenzyl bromide by conventional methods, to afford the 1,2,3,4-tetrahydro-4-isoquinolinol 2, which is cyclized to the spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] 5, wherein R is loweralkyl or benzyl and dealkylated or debenzylated to spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] 7, via the alkoxycarbonyl or phenoxycarbonyl derivative 6 wherein R1 is loweralkyl or phenyl, respectively. (See Reaction Scheme I).

Workup

  1. customTo prepare the parent ring system 7, i.e.

Sources & evidence

ORD record
ord-d6739179bcf74d7da43a5f53c94b6ddd
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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