1-methyl-1,2,3,4-tetrahydroisoquinoline Hydrochloride → HCID 23043040, compound

HRID 2165540Notes

Reaction equation

HRID 2165540 reaction equation
Cl.[CH3:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][NH:4]1.[N:13]([O-])=[O:14].[Na+]>O>[CH3:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[N:13]=[O:14]

Participants

4

Reactant 2

HCID 98129501-methyl-1,2,3,4-tetrahydroisoquinoline HydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 23043040HCID 23043040, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

21.5 g of 1-methyl-1,2,3,4-tetrahydro-isoquinolinehydrochloride (its preparation: Monatshefte, volume 53-54, 959 (1929) are dissolved in 50 cm3 water and to the solution a solution of 8.22 g of sodium nitrite in 25 cm3 water is added within 1 hour at 75° C. dropwise. The reaction mixture is cooled at 75° C. after stirring for 2 hours and it is extracted with 6×30 cm3 chloroform. The chloroform solution is washed with 50 cm3 water, dried and evaporated in vacuo. 19.2 g (93%) 1-methyl-2-nitroso-1,2,3,4-tetrahydro-isoquinoline are obtained as a brown oil which is used for the next step without further purification.

Workup

  1. additionis added within 1 hour at 75° C. dropwise
  2. extractionit is extracted with 6×30 cm3 chloroform
  3. washThe chloroform solution is washed with 50 cm3 water
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4ec6d675bfda4a5fb77da277eb77258e
Source dataset
uspto-grants-1990_07
Patent number
US04940716

Reaction notes

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