Sulfuric Acid → 8-Chloroisoquinolin-3-ol

HRID 1926234Notes

Reaction equation

HRID 1926234 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=1[CH2:9][NH:10][C:11](=[O:17])[CH:12](OC)OC.C([O-])(O)=O.[Na+]>>[Cl:6][C:7]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:8]=1[CH:9]=[N:10][C:11]([OH:17])=[CH:12]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 21419368N-[(2-Chlorophenyl)methyl]-2,2-dimethoxyacetamide

Product 1

HCID 1785153388-Chloroisoquinolin-3-ol

Conditions

Temperature
60 °C

Procedure

Concentrated sulfuric acid (18 M; 7.0 mL) was added to N-(2-chlorobenzyl)-2,2-dimethoxyacetamide (2.21 g, 9.07 mmol) at ambient temperature, and the solution was stirred overnight at ambient temperature and at 60° C. for 5 h. The cooled reaction mixture was added to ≈50 mL of ice, and the pH of the yellow mixture was adjusted to 7 with NaHCO3 solution. The yellow precipitate was filtered off, washed with water, and dried in vacuo, giving the title compound as yellow solid. The material was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ=11.13 (brs, 1H), 9.11 (s, 1H), 7.72 (d, J=8.4 Hz, 1H), 7.54 (dd, J=8.2, 7.2 Hz, 1H), 7.45 (dd, J=0.8, 7.2 Hz, 1H), 7.00 (s, 1H). MS(ES+): m/z=180.07/182.02 (100/38) [MH+]. HPLC: tR=2.45 min (polar—5 min, ZQ3).

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe yellow precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5d0d23157a204ce3b5da8ba1335e8c38
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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