Lithium Hydroxide → 3-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid

HRID 2089540Notes

Reaction equation

HRID 2089540 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)[CH:7]=[N:8][CH:9]=1)=[O:4].[Li+].[OH-]>C(O)C>[CH:10]1([N:6]2[C:5]([C:3]([OH:4])=[O:2])=[CH:9][N:8]=[CH:7]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 144976243-(1,2,3,4-Tetrahydronaphthalen-1-YL)-3H-imidazole-4-carboxylic acid methyl ester

Product 1

HCID 197940793-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester, which can be prepared as described in Example 2, (0.510 g, 1.990 mmol) in ethanol (20 mL) is added aqueous 4M LiOH (5 mL, 20 mmol) causing an immediate precipitate to form. After 3 hours, the mixture is evaporated to dryness, re-dissolved in a minimum amount of water, and the pH is adjusted to 6 with aqueous 2M HCl, causing a precipitate to form. The reaction is cooled to 0° C. and allowed to stand for 30 minutes. The precipitate is then filtered off and washed with cold phosphate buffer (pH 6). Upon standing, a solid precipitates out of the phosphate buffer which is filtered and combined with the initial precipitate to yield, upon drying under high vacuum, 3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid; MS: (ESI) m/z 243.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.77-1.96 (m, 2 H), 2.21-2.36 (m, 2 H), 2.87-2.95 (m, 1 H), 3.05 (dt, J=16.9, 5.8 Hz, 1 H), 6.57 (t, J=5.6 Hz, 1 H), 7.01 (d, J=7.8 Hz, 1 H), 7.18-7.26 (m, 1 H), 7.26-7.36 (m, 2 H), 7.55 (s, 1 H), 7.79 (d, J=1.0 Hz, 1 H).

Workup

  1. customto form
  2. customthe mixture is evaporated to dryness
  3. dissolutionre-dissolved in a minimum amount of water
  4. customto form
  5. waitto stand for 30 minutes
  6. filtrationThe precipitate is then filtered off
  7. washwashed with cold phosphate buffer (pH 6)
  8. customa solid precipitates out of the phosphate buffer which
  9. filtrationis filtered
  10. customto yield
  11. dry with materialupon drying under high vacuum, 3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid

Sources & evidence

ORD record
ord-84abd9f4012342cfa487636a6fefcd25
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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