Ammonia → HCID 68704306, compound

HRID 222113Notes

Reaction equation

HRID 222113 reaction equation
[NH:1]1[C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=[C:2]1[C:14]([O:16]C)=O.CO.[NH3:20].C(OCC)C>CN(C=O)C>[NH:1]1[C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=[C:2]1[C:14]([NH2:20])=[O:16]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 3283Diethyl EtherHCID 68711322HCID 68711322, compound

Product 1

HCID 68704306HCID 68704306, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-2-carboxylate L1 (0.44 mmol) in DMF (5 mL), MeOH (5 ml) and 30% aq NH3 (10 mL) was heated at 80° C. in a close vessel for 8 h. The solvent was evaporated, the residue was dissolved with DCM and washed with water. The organic layer was dried (Na2SO4) and concentrated to provide, after trituration with diethylether, the title compound (50% yield). ESI (+) MS: m/z 214 (MH+). 1H NMR: 2.69 (m, 2H), 2.84 (m, 2H), 6.72 (d, J=2.19, 1H), 7.08 (bs, 1H), 7.74 (d, J=5.12, 1H), 8.33-8.44 (2m, 2H), 12.01 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved with DCM
  3. washwashed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customto provide

Sources & evidence

ORD record
ord-44bd691dcac84c09b9373e588070b854
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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