Hydrochloric Acid → 388590-10-1

HRID 478704Notes

Reaction equation

HRID 478704 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:14])[N:3]=1.CO.[ClH:17]>O1CCCC1.CCOCC>[ClH:17].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH2:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:14])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18002680HCID 18002680, compound

Product 1

HCID 85802613388590-10-1

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-amino-6-cyano-3-methylisoquinoline (0.68 g) in 15 mL of tetrahydrofuran at room temperature under a nitrogen atmosphere was added 8.4 mL of 2M borane-methylsulfide complex in tetrahydrofuran and thereafter heated at 60° C. for 50 minutes. The reaction mixture was cooled in an ice bath and 7.5 mL of methanol was added slowly. After 15 minutes 18.8 mL of 1M hydrogen chloride in ether was added. The reaction mixture was allowed to warm to room temperature and stirred for an additional 16 hours. The solid was isolated to afford 0.34 g of 1-amino-6-(aminomethyl)-3-methylisoquinoline hydrogenchloride. The filtrate was purified using column chromatography (silica gel; methanol/ammonia=98/2) to yield an additional 0.15 g of 1-amino-6-(aminomethyl)-3-methylisoquinoline. ESI-MS: 188 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. temperatureto warm to room temperature
  3. customThe solid was isolated

Sources & evidence

ORD record
ord-b036e0fe06be4606aef9b861d57e39cc
Source dataset
uspto-grants-2003_11
Patent number
US06642253B2

Reaction notes

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