Sodium borohydride → HCID 67044913, compound

HRID 2367122Notes

Reaction equation

HRID 2367122 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([O-:14])=[O:13])=O)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[BH4-].[Na+]>C1COCC1.CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[O:13]2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 7176883HCID 7176883, compound

Product 1

HCID 67044913HCID 67044913, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(4-amino-3-nitrophenyl)carbonyl]benzoate (8.36 g, 27.8 mmol) in THF (100 mL) and methanol (30 mL) at 0° C. was added sodium borohydride (3.0 g, 79 mmol). The mixture was stirred for 40 min, and then unreacted hydride was quenched with 10% aqueous citric acid. The organic solvents were removed in vacuo. An orange solid precipitated from the resulting aqueous mixture. This solid was collected by filtration, rinsed with water, triturated with ether, and dried in vacuo. Desired 3-(4-amino-3-nitrophenyl)-2-benzofuran-1(3H)-one was obtained as a bright orange solid (5.23 g, 19.4 mmol, 69% yield). 1H NMR (400 MHz, d6-DMSO): 8.03 (d, 1H), 7.90 (d, 1H), 7.76 (t, 1H), 7.65-7.60 (m, 3H), 7.45 (d, 1H), 7.11 (dd, 1H), 6.99 (d, 1H), 6.66 (s, 1H); MS (EI) for C14H10N2O4: 303 (MNa+).

Workup

  1. customunreacted hydride was quenched with 10% aqueous citric acid
  2. customThe organic solvents were removed in vacuo
  3. customAn orange solid precipitated from the resulting aqueous mixture
  4. filtrationThis solid was collected by filtration
  5. washrinsed with water
  6. customtriturated with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-238db31a15344044a68436eb9e154f4d
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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