Hydrochloric Acid → HCID 178465843, compound

HRID 1595758Notes

Reaction equation

HRID 1595758 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:29]=[CH:28][C:24]2[NH:25][N:26]=[N:27][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.Cl>COCCO>[NH:25]1[C:24]2[CH:28]=[CH:29][C:21]([NH:20][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:18]#[N:19])=[CH:22][C:23]=2[N:27]=[N:26]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrileHCID 178507366HCID 178507366, compound

Product 1

HCID 178465843HCID 178465843, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1.07 mg (3.87 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 675 mg (5.00 mM) of 5-Aminobenzotriazole in 15 ml of 2-methoxyethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solution was made acetic by addition of concentrated HCl and the solid was collected, washed with water followed by ether and dried under vacuum at 80° C. The solid was taken up into 200 ml of methanol and 500 μl of 5 N sodium hydroxide and boiled for 20 minutes. To this heterogeneous mixture was added 100 ml of glacial acetic acid and the volume was reduced to a total of 100 ml by boiling. To the room temperature mixture, 500 ml of ice cold water was added and the solid was collected, washed with water followed by ether and dried under vacuum at 80° C. to yield 738 mg of Name as a brown solid: mass spectrum (electrospray, m/e): M+H 375.0, mp=Decomposed at 115° C.

Workup

  1. customthe solid was collected
  2. washwashed with water
  3. customdried under vacuum at 80° C
  4. additionTo this heterogeneous mixture was added 100 ml of glacial acetic acid
  5. additionTo the room temperature mixture, 500 ml of ice cold water was added
  6. customthe solid was collected
  7. washwashed with water
  8. customdried under vacuum at 80° C.
  9. customto yield 738 mg of Name as a brown solid
  10. customDecomposed at 115° C.

Sources & evidence

ORD record
ord-3a76488660544b7c96098e37cd1fc9fe
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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