Sulfamic Acid → 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acid

HRID 222110Notes

Reaction equation

HRID 222110 reaction equation
[C:1]1([C:7]2[NH:19][C:10]3=[C:11]4[C:16](=[CH:17][CH:18]=[C:9]3[C:8]=2[CH:20]=[O:21])[CH:15]=[N:14][CH:13]=[CH:12]4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)([OH:24])N.P([O-])(O)(O)=O.[Na+].Cl([O-])=O.[Na+]>O1CCOCC1.O>[C:1]1([C:7]2[NH:19][C:10]3=[C:11]4[C:16](=[CH:17][CH:18]=[C:9]3[C:8]=2[C:20]([OH:24])=[O:21])[CH:15]=[N:14][CH:13]=[CH:12]4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 866402502-Phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbaldehyde

Product 1

HCID 687095872-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-phenyl-1H-pyrrolo[2,3-f]isoquinoline-3-carbaldehyde G1 (0.55 mmol) in dioxane (6.8 mL) and water (2.4 mL), sulfamic acid (0.9 mmol) and sodium dihydrogen phosphate (2.33 mmol) were added. The mixture was cooled to 0° C. and sodium chlorite (0.95 mmol, dissolved in the minimum amount of water) was added. Other two additions of an equal amount of oxidant were made during 24 h of stirring, then the reaction was filtered and the solid product was washed with water and dried, resulting in 94% yield of the title compound. ESI (+) MS: m/z 289 (MH+); MS (ES−) 287. 1H NMR: 7.35-7.41 (m, 1H), 7.45-7.56 (m, 4H), 7.96 (d, J=9.00, 1H), 8.58 (d, J=9.00, 1H), 8.68 (d, J=5.17, 1H), 8.78 (d, J=5.17, 1H), 9.57 (s, 1H), 11.47 (bs, 1H), 13.54 (bs, 1H).

Workup

  1. additionwas added
  2. filtrationthe reaction was filtered
  3. washthe solid product was washed with water
  4. customdried

Sources & evidence

ORD record
ord-24884ce6b6a94ee2840105241ad5b4fe
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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