Water → HCID 68550475, compound

HRID 2359855Notes

Reaction equation

HRID 2359855 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][C:6]1[C:7]([NH2:16])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.B(Br)(Br)Br.O>ClCCl>[NH2:16][C:7]1[C:6]([CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]=2[OH:2])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 159538683-[(2-Methoxyphenyl)methyl]quinolin-2-amine

Product 1

HCID 68550475HCID 68550475, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(2-Methoxybenzyl)quinolin-2-amine (53 mg, 0.2 mmol) was mixed with boron tribromide solution in dichloromethane (1M, 0.4 mL, 0.4 mmol) in dichloromethane [sic; duplication] at −78° C. After thawing, the mixture was stirred for 12 hours at room temperature. The batch was mixed with water, extracted with dichloromethane and the combined organic phases were washed with sodium hydroxide solution (1M), water and saturated saline solution until neutral. After drying (sodium sulfate), the crude product was stirred with methyl tert-butyl ether and recrystallized from methanol/water (yield: 28 mg, 56%).

Workup

  1. extractionextracted with dichloromethane
  2. washthe combined organic phases were washed with sodium hydroxide solution (1M), water and saturated saline solution until neutral
  3. dry with materialAfter drying (sodium sulfate)
  4. stirringthe crude product was stirred with methyl tert-butyl ether
  5. customrecrystallized from methanol/water (yield: 28 mg, 56%)

Sources & evidence

ORD record
ord-3039bff50a6349d8bbf7cfa856c05e75
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

Loading…