Hydrochloric Acid → HCID 67974255, compound

HRID 1771475Notes

Reaction equation

HRID 1771475 reaction equation
[I:1][C:2]1[C:3](N)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.N([O-])=O.[Na+].[ClH:19]>O.Cl[Cu]>[Cl:19][C:3]1[C:2]([I:1])=[CH:11][C:10]2[C:5]([CH:4]=1)=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 57781065HCID 57781065, compound2×

Product 1

HCID 67974255HCID 67974255, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-iodo-7-methoxynaphthalen-2-amine (see Intermediate 6, product of step 3) (1.0 g, 3.34 mmol) in water (20 mL) and conc. HCl (20 mL) was added a solution of NaNO2 (230 mg, 3.34 mmol) in water (10 mL) dropwise at 0° C. and the reaction was stirred at 0° C. for 1 hour. Then CuCl (400 mg, 4.04 mmol) was added and the mixture was stirred at 20° C. for 2 hours. An aqueous/EtOAc workup was followed by purification by silica gel column (PE/EtOAc=100/1) to give 3-chloro-2-iodo-6-methoxynaphthalene (900 mg, yield 85%) as off-white solid. 1H NMR (CDCl3 300 MHz TMS): δ 8.29 (s, 1H), 7.84 (s, 1H), 7.60 (d, J=9.0 Hz, 1H), 7.13 (dd, J=9.0, 2.7 Hz, 1H), 6.99 (d, J=2.4 Hz, 1H), 3.91 (s, 3H).

Workup

  1. stirringthe mixture was stirred at 20° C. for 2 hours
  2. customAn aqueous/EtOAc workup was followed by purification by silica gel column (PE/EtOAc=100/1)

Sources & evidence

ORD record
ord-71868e09ad9e4be98c05f65e22ff75bb
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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