Hydrochloric Acid → HCID 66690508, compound

HRID 2209313Notes

Reaction equation

HRID 2209313 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[C:25]([CH2:27][N:28]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH:26]=1)[C:20]([O:22]C)=[O:21])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[OH-].[Na+].CO.CCOC(C)=O.Cl>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[C:25]([CH2:27][N:28]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[CH:26]=1)[C:20]([OH:22])=[O:21])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21584119Ethylacetate methanolHCID 66690529HCID 66690529, compound

Product 1

HCID 66690508HCID 66690508, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3,5-bis[[bis(2-pyridylmethyl)amino]methyl]benzoate (1 g, 1.8 mmol) was dissolved in MeOH (50 mL) and 10% solution of NaOH (5 mL) was added. The reaction mixture was refluxed for 2 h (reaction progress was monitored by TLC, Al2O3, MeOH/AcOEt 1:9 (v/v)). The reaction mixture was cooled to 0° C. followed by the addition of 10M HCl until pH=2 was reached followed by solvent evaporation under reduced pressure. Obtained yellow oily suspension was redissolved in water (50 mL) and TEA (3.6 g, 36 mmol) was added dropwise. Aqueous solution was extracted with DCM (2×50 mL) and organic layers were combined, evaporated and dried under high vacuum to obtain a product as a viscous oil. Yield: 1.1 g (95%). 1H NMR (500 MHz, CDCl3) δ 8.50 (m, 3H), 7.99 (d, J=1.3 Hz, 2H), 7.66 (d, J=8.7 Hz, 1H), 7.59 (m, 8H), 7.11 (m, 4H), 3.82 (s, 8H), 3.70 (s, 4H), 3.06 (q, J=7.3 Hz, 6H), 1.29 (t, J=7.3 Hz, 9H). 13C NMR (101 MHz, CDCl3) δ 170.2, 159.4, 148.9, 148.6, 138.8, 136.6, 136.5, 133.4, 132.7, 129.1, 122.9, 122.0, 77.3, 76.7, 60.1, 59.8, 58.5, 45.0, 8.5.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customwas reached followed by solvent evaporation under reduced pressure
  3. customObtained yellow oily suspension
  4. extractionAqueous solution was extracted with DCM (2×50 mL) and organic layers
  5. customevaporated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-586de495bbf04211a19f75a43f7f5ce8
Source dataset
uspto-grants-2016_06
Patent number
US09377466B2

Reaction notes

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