Sodium Hydroxide → 2-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

HRID 2425074Notes

Reaction equation

HRID 2425074 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:26])[C:10]2[O:16][C:15]3[C:17]([Cl:22])=[CH:18][C:19]([NH2:21])=[CH:20][C:14]=3[CH2:13][S:12](=[O:24])(=[O:23])[C:11]=2[CH:25]=1)=[O:6]>O.CO>[NH2:21][C:19]1[CH:18]=[C:17]([Cl:22])[C:15]2[O:16][C:10]3[C:9]([CH3:26])=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:25][C:11]=3[S:12](=[O:23])(=[O:24])[CH2:13][C:14]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 115596902-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 116317172-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium hydroxide (0.32 g, 7.13 mmol) in water (5 mL) was added to a solution of Example 1 (1 g, 2.71 mmol) in methanol (30 mL). The reaction mixture was stirred at 60° C. for 1.5 h, the solvent was removed under vacuum and water (20 mL) was added. The reaction mixture was acidified to pH 3 using 10% aqueous hydrochloric acid. The precipitate was filtered and washed with water, dried to obtain the title compound. Yield: 0.85 g, (89%); 1H NMR (DMSO-d6, 300 MHz): δ 2.61 (s, 3H, CH3), 5.66 (s, 2H, CH2), 6.64 (d, 2H, Ar), 8.03 (s, 1H, Ar), 8.12 (s, 1H, Ar); MS: m/e (ES−) 352 (M−1).

Workup

  1. customthe solvent was removed under vacuum and water (20 mL)
  2. additionwas added
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fcc28ce3c00143eeaeb90d24d064518c
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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