Water → 3-Aminomethyl-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinolin-2-ylamine

HRID 392183Notes

Reaction equation

HRID 392183 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:9]2[CH2:8][CH2:7][C:6]3[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=3[C:4]=2[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(OCC)(=O)C>C1COCC1>[NH2:13][CH2:12][C:11]1[C:2]([NH2:1])=[N:3][C:4]2[C:5]3[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=3[CH2:7][CH2:8][C:9]=2[C:10]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 226635122-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile

Product 1

HCID 102157313-Aminomethyl-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinolin-2-ylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of argon, a solution of 2-amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile (200 mg, 0.58 mmol) in THF (1 ml) is added slowly to a suspension of LiAlH4 (162 mg, 4.26 mmol) in THF (1 ml). After stirring for 2 h at room temperature, the reaction mixture is cooled to −20° C. and water (0.2 ml) is added. After 15 min, ethyl acetate is added and the mixture is filtered through Decalite. The organic phase is then separated, washed with water, and dried over sodium sulfate. Purification by flash chromatography (silica gel, methanol, dichloromethane) affords the title compound, MS: m/e=369.9 (M+H+), as a light yellow solid (53 mg, 26%).

Workup

  1. temperaturethe reaction mixture is cooled to −20° C.
  2. waitAfter 15 min
  3. filtrationthe mixture is filtered through Decalite
  4. customThe organic phase is then separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customPurification by flash chromatography (silica gel, methanol, dichloromethane)

Sources & evidence

ORD record
ord-e58ca9f83b63477d95cbf5d99ecb7fd1
Source dataset
uspto-grants-2004_10
Patent number
US06800650B2

Reaction notes

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