Ammonium Acetate → 6-Methoxy-7-methylisoquinolin-1-ylamine

HRID 1366754Notes

Reaction equation

HRID 1366754 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](OC1C=CC=CC=1)=[N:8][CH:7]=[CH:6]2.C([O-])(=O)C.[NH4+:25]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9]([NH2:25])=[N:8][CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 669417846-Methoxy-7-methyl-1-phenoxyisoquinoline

Product 1

HCID 669417806-Methoxy-7-methylisoquinolin-1-ylamineYield 80%

Conditions

Temperature
170 °C

Procedure

A mixture of the crude 6-methoxy-7-methyl-1-phenoxyisoquinoline (9 g, 33.96 mmol) and ammonium acetate (26 g) was melted with stirring at 170° C. for 5 h. The mixture was partitioned between aqueous sodium hydroxide (2 M) and ethyl acetate. The phases were separated and the organic phase extracted with dilute aqueous hydrochloric acid. The acidic aqueous phase was neutralized to pH 12 using sodium hydroxide (2M), extracted with ethyl acetate, dried (MgSO4) then dried in vacuo to give 6-methoxy-7-methylisoquinolin-1-ylamine (5.11 g, 27.18 mmol).

Workup

  1. customThe mixture was partitioned between aqueous sodium hydroxide (2 M) and ethyl acetate
  2. customThe phases were separated
  3. extractionthe organic phase extracted with dilute aqueous hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-02291a804e414101b7ad88ae25f49a65
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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