Acetic Anhydride → HCID 71209082, compound

HRID 1912634Notes

Reaction equation

HRID 1912634 reaction equation
[NH2:1][C:2]1[N:3]([CH:13]2[CH2:15][CH2:14]2)[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[C:11]#[N:12].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:11]([C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]([CH:13]2[CH2:15][CH2:14]2)[C:2]=1[NH:1][C:16](=[O:18])[CH3:17])#[N:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 71208778HCID 71208778, compound

Product 1

HCID 71209082HCID 71209082, compoundYield 71.5%

Procedure

A solution of 2-amino-1-cyclopropyl-4,5,6,7-tetrahydro-1H-indole-3-carbonitrile (3 g, 14.91 mmol) in acetic anhydride (24 ml, 254 mmol) was stirred at rt for 2.5 hours. The precipitate was filtered, washed with Ac2O, and dried to give N-(3-cyano-1-cyclopropyl-4,5,6,7-tetrahydro-1H-indol-2-yl)acetamide (2.5948 g, 10.66 mmol, 71.5% yield) as white solid. The filtrate was concentrated, suspended with Et2O, stirred, and filtered to give additional product (690 mg, 2.84 mmol, 19.03% yield) as light brown solid: 1H NMR (400 MHz, CHLOROFORM-d) δ=7.22 (br. s., 2 H), 2.98-2.86 (m, 1 H), 2.56 (t, J=5.9 Hz, 2 H), 2.49 (t, J=5.9 Hz, 2 H), 2.22 (s, 3 H), 1.88-1.65 (m, 4 H), 1.01-0.89 (m, 2 H), 0.88-0.76 (m, 2 H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with Ac2O
  3. customdried

Sources & evidence

ORD record
ord-027508267c0f46cd9b1a7eb5c28a5ea5
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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