Methanol → HCID 68412387, compound

HRID 1879985Notes

Reaction equation

HRID 1879985 reaction equation
C(OC(=O)[C:5]([C:7]1[CH:17]=[N:16][C:10]2[NH:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[CH:8]=1)=[CH2:6])C.[OH-:19].[Na+].[OH2:21].[CH3:22]O>>[N:16]1[C:10]2[NH:11][CH2:12][CH2:13][CH2:14][O:15][C:9]=2[CH:8]=[C:7]([CH:5]=[CH:6][C:22]([OH:21])=[O:19])[CH:17]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68415900HCID 68415900, compound

Product 1

HCID 68412387HCID 68412387, compoundYield 8%

Procedure

A solution of (6,7,8,9-tetrahydro-5-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylic acid ethyl ester (0.75 g, 3 mmol) in MeOH (30 mL) and aqueous NaOH (2 mL, 8 mmol, 4N) was refluxed for 23 hours. Upon cooling and addition of water (10 mL), the volatiles were evaporated; the aqueous solution was washed with CH2Cl2 and neutralized (1N HCl). The precipitate was filtered and dried to afford title product (55 mg, 8%). An additional 46 mg (7%) was obtained by extracting the aqueous filtrate with EtOAc. 1H NMR (300 MHz, DMSO-d6, 6): 12.10 (s, br 1H), 7.93 (d, J=1.9 Hz, 1H), 7.46 (d, J=1.9 Hz, 1H), 7.43 (d, J=16 Hz, 1H), 6.75 (t, br, J=3.4 Hz, 1H), 6.29 (d, J=16 Hz, 1H), 4.13 (t, J=6 Hz, 1H), 3.35 (m, 2H), 1.96 (m, 2H).

Workup

  1. temperatureUpon cooling
  2. customthe volatiles were evaporated
  3. washthe aqueous solution was washed with CH2Cl2 and neutralized (1N HCl)
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-ef8f023d2b1f4c20aef052dd70287f44
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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