Hydrochloric Acid → HCID 44176997, compound

HRID 910768Notes

Reaction equation

HRID 910768 reaction equation
C([C:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH:7]2[CH2:22][CH2:23][CH2:24][CH:6]2[C:5](=[O:25])[C:4]=1[C:26]([O-:28])=[O:27])C.[OH-].[Na+].Cl>C(O)C>[C:13]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[CH:3]=[C:4]([C:26]([OH:28])=[O:27])[C:5](=[O:25])[C:6]3[CH2:24][CH2:23][CH2:22][C:7]2=3)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131729185HCID 131729185, compound

Product 1

HCID 44176997HCID 44176997, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ethyl carboxylate (544 mg, 1.46 mmol) was dissolved in absolute ethanol (5 mL) and was treated with sodium hydroxide (1.75 mL, 1 N aqueous, 1.2 equiv). The mixture was stirred at ambient temperature for 2 hrs and then acidified (≦pH 4) with hydrochloric acid (1 N aqueous). The precipitate that formed was collected and washed successively with water and absolute ethanol, providing the title compound as a white solid: 1H-NMR (400 MHz, CDCl3) δ 8.52 (1H, s), 7.63 (2H, d, J=8.2 Hz) 7.57 (2H, d, J=7.0 Hz), 7.46 (2H, t, J=7.1 Hz), 7.18 (2H, d, J=8.2 Hz), 5.18 (2H, s), 2.99-2.93 (4H, m), 2.22-2.15 (2H, m) ppm; high resolution mass spectrum (ES+) m/z 346.1442 [(M+H)+; calculated for C22H20NO3: 346.1438].

Workup

  1. customThe precipitate that formed
  2. customwas collected
  3. washwashed successively with water and absolute ethanol

Sources & evidence

ORD record
ord-79a935036284449b85eba2d69cf4775f
Source dataset
uspto-grants-2011_09
Patent number
US08022215B2

Reaction notes

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