Hydrochloric Acid → HCID 67520377, compound

HRID 1925308Notes

Reaction equation

HRID 1925308 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[C:8](N)=[CH:7][CH:6]=1)=[O:4].Cl.N([O-])=O.[Na+].[I-:22].[K+]>C1COCC1.O.CCOC(C)=O>[OH:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=[C:8]2[I:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 67520047HCID 67520047, compound

Product 1

HCID 67520377HCID 67520377, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl-4-amino-6-hydroxy-1-naphthoate (0.500 g, 2.30 mmol) in THF (2.5 mL) was cooled to 0° C. and 3 N HCl (5.0 mL) was added. A solution of sodium nitrite (0.175 g, 2.53 mmol) in water (1.2 mL) was added and the mixture stirred at 0° C. for 15 min. A solution of potassium iodide (0.764 g, 4.60 mmol) in water (1.2 ml) was added and the mixture was stirred at 0° C. for 1 h. EtOAc was added and the solution was poured into water. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford a red-brown oil. This material was purified via column chromatography on silica gel (eluting with 0-50% EtOAc-hexane) to afford methyl 6-hydroxy-4-iodo-1-naphthoate as a tan solid. MS (ESI, pos. ion) m/z: 328.8 (M+H). Mass Calc'd for C12H9IO3: 328.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 h
  2. customThe aqueous phase was separated
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a red-brown oil
  9. customThis material was purified via column chromatography on silica gel (eluting with 0-50% EtOAc-hexane)

Sources & evidence

ORD record
ord-e9b28d9f92f54a7e820cb85803a6c0f7
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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