Hydrochloric Acid → HCID 67421363, compound

HRID 1987370Notes

Reaction equation

HRID 1987370 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:16]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:6][CH:5]=1.O.[OH-].[Na+].Cl>CO>[CH3:30][C:29]1[C:24]([CH:12]2[CH2:13][CH2:14][CH2:15][CH:16]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[N:11]2[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=2)=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67422067HCID 67422067, compound

Product 1

HCID 67421363HCID 67421363, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (0.420 g, 1.01 mmol) in MeOH (5 mL) was added water (5 mL) and solid NaOH (0.448 g, 11.21 mmol). The resultant mixture was heated to reflux overnight then cooled to room temperature. The mixture was adjusted to pH ˜5 with 6 N HCl (˜2 mL) and extracted with CH2Cl2 (5×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated and provided 0.440 g (quantitative yield) of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid as a white solid. 1H NMR (CDCl3) δ 1.80-2.05 (m, 6H), 2.42 (s, 6H), 3.83 (br s, 2H), 4.55 (br s, 2H) 6.79 (d, 2H, J=8.1 Hz), 7.02 (dd, 2H, J=7.5, 5.1 Hz), 7.34 (d, 2H, J=7.5 Hz), 7.65 (d, 2H, J=7.8 Hz), 8.42 (d, 2H, J=3.9 Hz); ES-MS m/z 402 (M+H).

Workup

  1. temperatureto reflux overnight
  2. extractionextracted with CH2Cl2 (5×20 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4caf7cf672d74ff3a98df250e82363dc
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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