Hydrochloric Acid → HCID 21445357, compound

HRID 918182Notes

Reaction equation

HRID 918182 reaction equation
[ClH:1].N[C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH:9]([CH3:20])[N:10]3[C:15]=2[C:14]=1[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11]3.N([O-])=O.[Na+]>O>[Cl:1][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH:9]([CH3:20])[N:10]3[C:15]=2[C:14]=1[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11]3

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13094348HCID 13094348, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21445357HCID 21445357, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 75 ml. of 6N hydrochloric acid and 10-amino-6,7-dihydro-5-methyl-1-oxo-benzo[ij]quinolizine-2-carboxylic acid (12.9 g., 0.05 mole) is diazotized at 5 to 10° C. with sodium nitrite (4.14 g., 0.06 mole) dissolved in about 10 ml. of water. The cold mixture is filtered, then it is added to a mixture of cuprous chloride (19.7 g., 0.1 mole) and concentrated hydrochloric acid (150 ml.) while maintaining the temperature below 20° C. After stirring 1 hour the mixture is diluted with water to provide a creamy-white solid which is collected by filtration. Two recrystallizations from N,N-dimethyl formamide provide 10-chloro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. 219.5°-222° C.

Workup

  1. additionA mixture of 75 ml
  2. dissolutiondissolved in about 10 ml
  3. filtrationThe cold mixture is filtered
  4. temperaturewhile maintaining the temperature below 20° C
  5. customto provide a creamy-white solid which
  6. filtrationis collected by filtration
  7. customTwo recrystallizations from N,N-dimethyl formamide

Sources & evidence

ORD record
ord-487b8804870849f4bc3fb49893677470
Source dataset
uspto-grants-1976_07
Patent number
US03969463

Reaction notes

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