Formamide → 6-Hydroxy-3,4-dihydroisoquinoline-2(1H)-carbaldehyde

HRID 597202Notes

Reaction equation

HRID 597202 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[CH:13](N)=[O:14]>O>[CH:13]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=2)[CH2:9]1)=[O:14]

Participants

4

Reactant 2

HCID 713FormamideHCID 133617991,2,3,4-Tetrahydroisoquinolin-6-ol--hydrogen bromide (1/1)

Product 1

HCID 214470386-Hydroxy-3,4-dihydroisoquinoline-2(1H)-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

46.0 g of 1,2,3,4-tetrahydro-6-hydroxy-isoquinoline-hydrobromide are reacted with 85 ml of formamide for 1 hour at 140° C. with stirring. After cooling to 100° C., 216 ml of water are added, whereby the reaction product crystallizes. 34.0 g of 2-formyl-1,2,3,4-tetrahydro-6-hydroxy-isoquinoline are obtained. m.p. = 185.5° - 186° C. (ethanol).

Workup

  1. customwhereby the reaction product crystallizes

Sources & evidence

ORD record
ord-3aa79ced6f8a404c8534bcfc361a94b0
Source dataset
uspto-grants-1977_03
Patent number
US04013663

Reaction notes

Loading…