Triethylamine → HCID 15617228, compound

HRID 2351613Notes

Reaction equation

HRID 2351613 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>[Pd].O1CCCC1>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][C:4]2[C:5]([NH:10][CH2:11][CH:12]([OH:13])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:6][CH:7]=[CH:8][CH:9]=2)=[O:26])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 14390523HCID 14390523, compound

Product 1

HCID 15617228HCID 15617228, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of α-[(3-nitro-2-pyridinylamino)methyl]benzene methanol (30.8 g, 0.12 mole) and 5% palladium on carbon catalyst in 450 ml of tetrahydrofuran was hydrogenated in a large glass Parr bottle at room temperature. The reaction mixture was dried over magnesium sulfate and filtered through a Celite pad. p-Chlorobenzoyl chloride (15.1 ml, 0.12 mole) and triethylamine (16.5 ml, 0.12 mole) were added simultaneously dropwise to the stirred filtrate at 12°-15° C. (ice-water bath) and the mixture was allowed to stir at ambient temperature overnight. The reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was partitioned between methylene chloride and water. The methylene chloride layer was separated and extracted with water (1×), 5% potassium hydroxide (2×), and water (2×). The methylene chloride layer was separated, dried, and evaporated to dryness. The residue was purified on a silica gel column (400 g) by eluting with 50% ethyl acetate/50% hexanes. Total recovery: 18.2 g (41.6% yield). A 5-g sample was recrystallized from ethyl acetate/hexanes to give 2.71 g of solid, mp. 157°-159° C.

Workup

  1. customwas hydrogenated in a large glass Parr bottle at room temperature
  2. dry with materialThe reaction mixture was dried over magnesium sulfate
  3. filtrationfiltered through a Celite pad
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was partitioned between methylene chloride and water
  7. customThe methylene chloride layer was separated
  8. extractionextracted with water (1×), 5% potassium hydroxide (2×), and water (2×)
  9. customThe methylene chloride layer was separated
  10. customdried
  11. customevaporated to dryness
  12. customThe residue was purified on a silica gel column (400 g)
  13. washby eluting with 50% ethyl acetate/50% hexanes
  14. customA 5-g sample was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-687f152f2d134b508455321eb11ddca1
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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