Hydrochloric Acid → 1-Methyl-1,2,3,4-tetrahydroquinolin-7-ol

HRID 1731610Notes

Reaction equation

HRID 1731610 reaction equation
O.Cl.Cl.[CH3:4][N:5]1[C:14]2[C:9](=[CH:10][C:11](N=O)=[C:12]([OH:15])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1>CO>[CH3:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13750926HCID 13750926, compound

Product 1

HCID 137509151-Methyl-1,2,3,4-tetrahydroquinolin-7-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(0.093 mole) was dissolved in a mixture of methanol 105 ml., water 70 ml., and concentrated hydrochloric acid 35 ml. and was filtered into a 500 ml. conical flask. The solution was well cooled to maintain a temperature between 0° and 5° and was rapidly stirred whilst a 10% aqueous solution of sodium nitrite 67 ml. (5% excess) mixed with methanol 67 ml. was slowly dripped in over half an hour and then stirred for another hour. The precipitate was filtered, washed with cold, dilute hydrochloric acid and air-dried to give 11.7 g. (56%) of yellow-brown fine crystals of 1-methyl-1,2,3,4-tetrahydro-6-nitroso-7-hydroxyquinoline hydrochloride.

Workup

  1. filtrationand was filtered into a 500 ml
  2. temperatureThe solution was well cooled
  3. temperatureto maintain a temperature between 0° and 5°
  4. addition(5% excess) mixed with methanol 67 ml
  5. customwas slowly dripped in over half an hour
  6. stirringstirred for another hour
  7. filtrationThe precipitate was filtered
  8. washwashed with cold, dilute hydrochloric acid
  9. customair-dried
  10. customto give 11.7 g

Sources & evidence

ORD record
ord-c70a85260bfc46eeb9eeb338cde7ecf0
Source dataset
uspto-grants-1986_11
Patent number
US04622400

Reaction notes

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