Hydrochloric Acid → HCID 25061491, compound

HRID 2244080Notes

Reaction equation

HRID 2244080 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[C:5]([C:25]#N)=[CH:4][N:3]=1.Cl.[OH-:28].[Na+].[OH2:30]>C1COCC1>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[C:5]([C:25]([OH:30])=[O:28])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 25061240HCID 25061240, compound

Product 1

HCID 25061491HCID 25061491, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-amino-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-isoquinoline-4-carbonitrile (0.15 g, 0.44 mmol) in THF (2 mL) and H2O (2 mL) is treated with concentrated HCl (10 mL). The reaction mixture is microwaved at 150° C. for 1.5 h. The reaction mixture is then treated with 5 M NaOH until pH=8. The crystals formed are collected by vacuum filtration, and dried to afford 0.07 g (44%) of 1-amino-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-isoquinoline-4-carboxylic acid. LC/MS m/z=364 [M+H]+, RT=2.12 min.

Workup

  1. customThe reaction mixture is microwaved at 150° C. for 1.5 h
  2. customThe crystals formed
  3. filtrationare collected by vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-a970851ed3164cbc949adbfa7815b3c3
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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