Sodium Hydroxide → 4-[2,4-Dioxo-3,4-dihydro-1H-naphtho[2,1-b][1,4]diazepin-5(2H)-yl]benzoic acid

HRID 1049759Notes

Reaction equation

HRID 1049759 reaction equation
[O:1]=[C:2]1[CH2:8][C:7](=[O:9])[N:6]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=2)[C:5]2[CH:21]=[CH:22][C:23]3[C:28]([C:4]=2[NH:3]1)=[CH:27][CH:26]=[CH:25][CH:24]=3.[OH-].[Na+]>C(O)C.O>[O:1]=[C:2]1[CH2:8][C:7](=[O:9])[N:6]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:19][CH:20]=2)[C:5]2[CH:21]=[CH:22][C:23]3[C:28]([C:4]=2[NH:3]1)=[CH:27][CH:26]=[CH:25][CH:24]=3

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117699155Ethyl 4-[2,4-dioxo-3,4-dihydro-1H-naphtho[2,1-b][1,4]diazepin-5(2H)-yl]benzoate

Product 1

HCID 1176991814-[2,4-Dioxo-3,4-dihydro-1H-naphtho[2,1-b][1,4]diazepin-5(2H)-yl]benzoic acidYield 82.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 4-[2,4-Dioxo-3,4-dihydro-1H-naphtho[2,1-b][1,4]diazepin-5(2H)-yl]benzoate (1.19 g, 3.18 mmol) obtained in Example 102, (3), and 8 N aqueous sodium hydroxide (1.00 mL, 8.00 mmol) were stirred at room temperature in ethanol (10 mL) and water (5 mL). After the disappearance of the starting materials was confirmed, a post-treatment was performed in a conventional manner to obtain the title compound (905 mg, yield 82%).

Sources & evidence

ORD record
ord-5cdea0e6f2fc4f49bfd6c5beec2c00dc
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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