Methanol → Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl ester

HRID 1749196Notes

Reaction equation

HRID 1749196 reaction equation
[Si](C=[N+]=[N-])(C)(C)[CH3:2].C[Si](C)(C)C.[NH2:13][C:14]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[C:16]([F:26])[C:15]=1[F:27].CO>O1CCCC1>[CH3:2][O:19][C:18](=[O:20])[C:17]1[CH:21]=[C:22]([N+:23]([O-:25])=[O:24])[C:14]([NH2:13])=[C:15]([F:27])[C:16]=1[F:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 162440884-Amino-2,3-difluoro-5-nitrobenzoic acidHCID 86616138Tetramethylsilane (TMS) diazomethane

Product 1

HCID 2759749Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 M solution of tetramethylsilane (TMS) diazomethane in hexanes (6.88 ml, 13.75 mmol) was added to a suspension of 4-amino-2,3-difluoro-5-nitrobenzoic acid (2.00 g, 9.17 mmol) in 25 ml of 4:1 Tetrahydrofuran (THF):MeOH at 0° C. under nitrogen atmosphere. Upon completion of addition, reaction mixture was warmed to room temperature. After 0.5 hours, excess TMS diazomethane was destroyed by the careful addition of acetic acid. The reaction was then concentrated under reduced pressure and dried in vacuo 1.95 g (92%) of pure desired product: MS APCI (−) m/z 231 (M−1) detected.

Workup

  1. customat 0° C.
  2. additionUpon completion of addition, reaction mixture
  3. customexcess TMS diazomethane was destroyed by the careful addition of acetic acid
  4. concentrationThe reaction was then concentrated under reduced pressure
  5. dry with materialdried in vacuo 1.95 g (92%) of pure desired product

Sources & evidence

ORD record
ord-a962f70c3bd446b19722536292c5f379
Source dataset
uspto-grants-2015_10
Patent number
US09156795B2

Reaction notes

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