7-nitro-3,4-dihydro-2H-naphthalen-1-one oxime → 1,2,3,4-Tetrahydronaphthalene-1,7-diamine

HRID 423917

反応式

HRID 423917 の反応式
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[N:14]O)=[CH:6][CH:5]=1)([O-])=O>CO>[CH:11]1([NH2:14])[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1

参加物

3

反応物 1

HCID 3000317-nitro-3,4-dihydro-2H-naphthalen-1-one oxime

生成物 1

HCID 212566931,2,3,4-Tetrahydronaphthalene-1,7-diamine収率 96%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

7-Nitro-3,4-dihydro-2H-naphthalen-1-one oxime (274 mg, 1.33 mmol) was dissolved in methanol (10 mL) and the flask was flushed with N2 (g). 10% Pd—C (50 mg) was added and the reaction was stirred under H2 (1 atm) at room temperature overnight. The reaction was filtered and the filtrate was concentrated to yield 1,2,3,4-tetrahydro-naphthalene-1,7-diamine (207 mg, 96%). 1H NMR (400 MHz, DMSO-d6) δ 6.61-6.57 (m, 2H), 6.28 (dd, J=8.0, 2.4 Hz, 1H), 4.62 (s, 2H), 3.58 (m, 1H), 2.48-2.44 (m, 2H), 1.78-1.70 (m, 2H), 1.53-1.37 (m, 2H).

後処理

  1. customthe flask was flushed with N2 (g)
  2. addition10% Pd—C (50 mg) was added
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-55368aae07b1434ea0ab95af2b576d9b
出典データセット
uspto-grants-2012_01
特許番号
US08101767B2

関連ノート

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