Ammonium formate → Methyl 3,4-diamino-2-methylbenzoate

HRID 906099노트

반응식

HRID 906099 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-])=O.C([O-])=O.[NH4+]>O1CCCC1.O.[Fe]>[NH2:13][C:3]1[C:4]([CH3:12])=[C:5]([CH:10]=[CH:11][C:2]=1[NH2:1])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 67404328HCID 67404328, 화합물

생성물 1

HCID 67403564Methyl 3,4-diamino-2-methylbenzoate수율 98%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-amino-2-methyl-3-nitrobenzoate (1.10 g, 5.22 mmol) in tetrahydrofuran (75 mL) and water (25 mL) was added ammonium formate (6.6 g, 104 mmol) and iron powder (2.92 g, 52.2 mmol). This mixture was refluxed for 12 hours then filtered and the filter cake rinsed with ethyl acetate. The filtrate layers were separated and the organic layer was dried (magnesium sulfate), filtered and concentrated to give 0.92 g (98% yield) of crude methyl 3,4-diamino-2-methylbenzoate, which was used without further purification. 1H NMR (400 MHz, d6-DMSO): 7.05 (d; 1H), 6.40 (d, 1H), 3.69 (s, 3H), 2.29 (s, 3H). MS (EI) for C9H12N2O2: 181 (MH+).

후처리

  1. temperatureThis mixture was refluxed for 12 hours
  2. filtrationthen filtered
  3. washthe filter cake rinsed with ethyl acetate
  4. customThe filtrate layers were separated
  5. dry with materialthe organic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3eca5cd7bf5f44cabea27c30ec8fa22a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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