Tetrahydrofuran → HCID 59203847, compound

HRID 2241802Notes

Reaction equation

HRID 2241802 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][N:3]=1.[OH:10][C:11]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=1[NH2:13].C(N(CC)CC)C.C1C[O:30]CC1>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH:13][C:12]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]=2[OH:10])=[O:30])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 99421632-Amino-5-methoxyphenol

Product 1

HCID 59203847HCID 59203847, compound

Procedure

6-Chloronicotinyl chloride (2.0 g, 11.4 mmol) in THF (10 mL) was added dropwise to a mixture of 2-hydroxy-4-methoxyaniline (1.58 g) and triethylamine (1.8 mL) in THF (20 mL) at r.t. The reaction was stirred at r.t for 30 minutes and was then heated to reflux for 5 minutes. After cooling to r.t. the solid was collected, rinsed with water, dried (under vacuum over P2O5), to give the title compound (1.77 g) as an orange solid. 1H NMR δ ppm 9.78 (br. s, 1H) 9.63 (br. s, 1H) 8.94 (d, 1H) 8.34 (dd, 1H) 7.68 (d, 1H) 7.34 (d, 1H) 6.49 (d, 1H) 6.42 (dd, 1H) 3.71 (s, 3H); MS m/z (M+H) 279, 281; (M−H) 277, 279.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 5 minutes
  3. customwas collected
  4. washrinsed with water
  5. dry with materialdried (under vacuum over P2O5)

Sources & evidence

ORD record
ord-f84ccbfe89c146a9bab2602423914949
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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