Hydrochloric Acid → HCID 22903484, compound

HRID 1489088Notes

Reaction equation

HRID 1489088 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:42])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:41])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][N:30]4C(=O)C5=CC=CC=C5C4=O)=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:43]=1.O.NN.O.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:42])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:41])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][NH2:30])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:43]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 22903475HCID 22903475, compound

Product 1

HCID 22903484HCID 22903484, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-chloro-1-{6-[2-(2-phthalimidoethoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g) in ethanol (5 ml) is added hydrazine monohydrate (0.03 ml), and the mixture is refluxed for one hour, and cooled. To the mixture is added water, and the mixture is made acidic with diluted hydrochloric acid, and washed with diethyl ether. The aqueous layer is made basic with aqueous sodium hydroxide solution, and extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is crystallized from diethyl ether to give 7-chloro-1-{6-[2-(2-aminoethoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (110 mg) as white powder.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. temperaturecooled
  3. washwashed with diethyl ether
  4. extractionextracted with dichloromethane
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-ac7b72656680400ea1aa345bb500284c
Source dataset
uspto-grants-1997_10
Patent number
US05677299

Reaction notes

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