Hydrochloric Acid → HCID 18933501, compound

HRID 1598017Notes

Reaction equation

HRID 1598017 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH2:22])[CH:16]=1.C(O[CH2:27][CH3:28])(=O)C.[ClH:29]>C1(O)C=CC=CC=1.O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([C:2]4[C:27]5[C:28](=[CH:11][C:6]([Cl:29])=[CH:7][CH:8]=5)[N:5]=[CH:4][CH:3]=4)[NH2:22])[CH:16]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 8857Ethyl AcetateHCID 151331,3-Benzenedimethanamine

Product 1

HCID 18933501HCID 18933501, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 996PhenolSolvent

Procedure

3.96 g of 4,7-dichloroquinoline and 1.36 g of α,α'-diamino-m-xylene are reacted at 140° C. in 4 g of phenol under argon for 24 hours. After cooling the mixture is treated with 20 ml of ethyl acetate and 30 ml of water and adjusted to pH 1 by adding a small amount of concentrated hydrochloric acid. The product which thereby crystallizes out is filtered off under suction and triturated in 200 ml of 2N NaOH and 50 ml of ethyl acetate. The separated crystalline amine is suspended in 80 ml of 0.5N HCl and brought into solution on a steam bath by the addition of ethanol (75 ml). 3.14 g of the dihydrochloride crystallize out upon cooling, m.p.:>250° C.

Workup

  1. temperatureAfter cooling the mixture
  2. customThe product which thereby crystallizes out
  3. filtrationis filtered off under suction
  4. customtriturated in 200 ml of 2N NaOH
  5. additionbrought into solution on a steam bath by the addition of ethanol (75 ml)
  6. custom3.14 g of the dihydrochloride crystallize out
  7. temperatureupon cooling

Sources & evidence

ORD record
ord-9254911905ba44c39a782083be5f716d
Source dataset
uspto-grants-1998_04
Patent number
US05736557

Reaction notes

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