Sodium Hydroxide → HCID 58118607, compound

HRID 1690798Notes

Reaction equation

HRID 1690798 reaction equation
[CH3:1][O:2][C:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH:11]([C:16]([O:18]C)=[O:17])[CH2:10][CH2:9][C:8]=2[N:7]=1)([CH3:5])[CH3:4].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH:11]([C:16]([OH:18])=[O:17])[CH2:10][CH2:9][C:8]=2[N:7]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58118600HCID 58118600, compound

Product 1

HCID 58118607HCID 58118607, compoundYield 157.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4-mL vial with stir bar was charged with methyl 2-(2-methoxypropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylate (16 mg, 0.061 mmol), methanol (450 μL) and 4M sodium hydroxide (150 μL, 0.61 mmol). The mixture was stirred at room temperature for 1 hour then quenched into 1M NaH2PO4 (2 mL) and 1M citric acid was added to obtain pH 4-5. The mixture was extracted with EtOAc (3 mL×3), dried (Na2SO4), filtered and evaporated to obtain a colorless oil (24 mg), which was used directly in the next step. m/z=250.3 (M+H)+. 1H NMR (400 MHz; CD3OD) δ 8.32 (d, J=8.3 Hz, 1H), 7.83 (d, J=8.3 Hz, 1H), 3.3.0 (s, 3H), 3.29-3.15 (m, 4H), 3.00-2.90 (m, 1H), 2.41-2.31 (m, 1H), 2.17-2.04 (m, 1H), 2.04 (s, 2H), 1.66 (s, 6H).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. customthen quenched into 1M NaH2PO4 (2 mL) and 1M citric acid
  3. additionwas added
  4. customto obtain pH 4-5
  5. extractionThe mixture was extracted with EtOAc (3 mL×3)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-89769f3350bb448287649ca99177ca20
Source dataset
uspto-grants-2012_04
Patent number
US08153651B2

Reaction notes

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