Anthranilic Acid → HCID 69510389, compound

HRID 969681

Reaction equation

HRID 969681 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]=O.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.CCOC(C)=O.CO>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

9

Reactant 4

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 221391207-Fluoro-1H-indole-3-carbaldehyde

Product 1

HCID 69510389HCID 69510389, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-fluoro-1H-indole-3-carbaldehyde (200 mg, 1.23 mmol), 2-amino-benzoic acid (168 mg, 1.23 mmol) and p-toluenesulfonic acid (20 mg, 10% W/W) was heated a reflux in toluene (5 mL) for 4 h. The mixture was cooled to RT and diluted with CH2Cl2. NaBH4 (51.4 mg) was added followed by MeOH (2 mL). The mixture was stirred for 1 h. The reaction mixture was diluted with EtOAc (10 mL) and extracted with water (2×10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo affording the titled compound as a light yellow solid. ESI MS: (M−1)=283. Calc'd for C16H13FN2O2-284.29.

Workup

  1. temperaturewas heated
  2. extractionextracted with water (2×10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdf5aee18ed2430f9455e6152b5c501a
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Linked notes

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